Novel substituted phenylketoenols

ABSTRACT

The invention relates to novel phenyl-substituted cyclic ketoenols of the formula (I)  
                 
 
     in which  
     A, B, G, X, Y, Z and W are each as defined in the description,  
     to processes and intermediates for their preparation and to their use as pesticides and herbicides.

[0001] The invention relates to novel phenyl-substituted cyclicketoenols, to a plurality of processes and intermediates for theirpreparation and to their use as pesticides and herbicides.

[0002] It is already known that certain phenyl-substituted cyclicketoenols are active as insecticides, acaricides and/or herbicides.

[0003] 1H-Arylpyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334,EP-A-596 298, EP-A-613 884, EP-A-613 885, DE-44 40 594, DE-196 49 665,WO 94/01 997, WO 95/01 358, WO 95/20 572, EP-A-668 267, WO 95/26 954, WO96/25395, WO 96/35 664, WO 97/01 535 and WO 97/02 243) and their use aspesticides and, of some of them, as herbicides, are known.

[0004] However, the herbicidal, acaricidal and insecticidal activityand/or spectrum of activity and/or plant safety of these compounds, inparticular with respect to crop plants, is not always satisfactory.

[0005] This invention, accordingly, provides novel compounds of theformula (I)

[0006] in which

[0007] W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl,alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy or represents phenyl,phenoxy, phenylthio, phenylalkoxy or phenylalkylthio, each of which isoptionally substituted,

[0008] X represents halogen, alkyl, alkenyl, alkinyl, alkoxy,alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, cyano,nitro or represents phenyl, phenoxy, phenylthio, phenylalkyloxy orphenylalkylthio, each of which is optionally substituted,

[0009] Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro,

[0010] Z represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, hydroxyl, cyano, nitro or represents phenoxy,phenylthio, 5- or 6-membered hetaryloxy, 5- or 6-membered hetarylthio,phenylalkyloxy or phenylalkylthio, each of which is optionallysubstituted,

[0011] A represents alkyl or optionally substituted phenyl,

[0012] B represents hydrogen or alkyl,

[0013] G represents hydrogen (a) or one of the radicals

[0014] in which

[0015] E represents a metal ion equivalent or an ammonium ion,

[0016] L represents oxygen or sulphur,

[0017] M represents oxygen or sulphur,

[0018] R¹ represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl orpolyalkoxyalkyl, each of which is optionally substituted by halogen orcyano, or represents cycloalkyl or heterocyclyl, each of which isoptionally substituted by halogen, alkyl or alkoxy, or representsphenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, each ofwhich is optionally substituted,

[0019] R² represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl,each of which is optionally substituted by halogen or cyano, orrepresents cycloalkyl, phenyl or benzyl, each of which is optionallysubstituted,

[0020] R³, R⁴ and R⁵ independently of one another each represent alkyl,alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio orcycloalkylthio, each of which is optionally substituted by halogen, orrepresent phenyl, benzyl, phenoxy or phenylthio, each of which isoptionally substituted,

[0021] R⁶ and R⁷ independently of one another each represent hydrogen,represent alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each of whichis optionally substituted by halogen or cyano, represent phenyl orbenzyl, each of which is optionally substituted, or together with thelinking N atom form a cycle which optionally contains oxygen or sulphurand which is optionally substituted.

[0022] The compounds of the formula (I) can be present, depending, interalia, on the nature of the substituents, as optical isomers or isomermixtures of differing composition which, if appropriate, can beseparated in a customary manner. Both the pure isomers and the isomermxtures, their preparation and use, and compositions comprising them arepart of the subject matter of the present invention. In the following,for simplicity, however, compounds of the formula (I) are alwaysreferred to, although both pure compounds and, if appropriate, mixtureshaving different proportions of isomeric compounds are intended.

[0023] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-a) to (I-g)result:

[0024] in which

[0025] A, B, E, L, M, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are eachas defined above.

[0026] Furthermore, it has been found that the novel compounds of theformula (I) are obtained by one of the processes described below:

[0027] (A) Compounds of the Formula (I-a)

[0028] in which

[0029] A, B, W, X, Y and Z are each as defined above,

[0030] are obtained when

[0031] compounds of the formula (II)

[0032] in which

[0033] A, B, W, X, Y and Z are each as defined above, and

[0034] R⁸ represents alkyl (preferably C₁-C₆-alkyl),

[0035] are intramolecularly condensed in the presence of a diluent andin the presence of a base.

[0036] Furthermore, it has been found

[0037] (B) that the compounds of the formula (I-b) shown above in whichR¹, A, B, W, X, Y and Z are each as defined above are obtained whencompounds of the formula (I-a) shown above in which A, B, W, X, Y and Zare each as defined above,

[0038] α) are reacted with acyl halides of the formula (III)

[0039] in which

[0040] R¹ is as defined above and

[0041] Hal represents halogen (in particular chlorine or bromine) or

[0042] β) are reacted with carboxylic anhydrides of the formula (IV)

R¹—CO—O—CO—R¹  (IV)

[0043] in which

[0044] R¹ is as defined above,

[0045] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0046] (C) that the compounds of the formula (I-c) shown above in whichR², A, B, W, M, X, Y and Z are each as defined above and L representsoxygen are obtained when compounds of the formula (I-a) shown above inwhich A, B, W, X, Y and Z are each as defined above,

[0047] are reacted with chloroformic esters or chloroformic thioestersof the formula (V)

R²—M—CO—Cl  (V)

[0048] in which

[0049] R² and M are each as defined above,

[0050] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0051] (D) that compounds of the formula (I-c) shown above in which R²,A, B, W, M, X, Y and Z are each as defined above and L representssulphur are obtained when compounds of the formula (I-a) shown above inwhich A, B, W, X, Y and Z are each as defined above,

[0052] are reacted with chloromonothioformic esters orchlorodithioformic esters of the formula (VI)

[0053] in which

[0054] M and R² are each as defined above,

[0055] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0056] (E) that compounds of the formula (I-d) shown above in which R³,A, B, W, X, Y and Z are each as defined above are obtained whencompounds of the formula (I-a) shown above in which A, B, W, X, Y and Zare each as defined above,

[0057] are reacted with sulphonyl chlorides of the formula (VII)

R³—SO₂—Cl  (VII)

[0058] in which

[0059] R³ is as defined above,

[0060] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0061] (F) that compounds of the formula (I-e) shown above in which L,R⁴, R⁵, A, B, W, X, Y and Z are each as defined above are obtained whencompounds of the formula (I-a) shown above in which A, B, W, X, Y and Zare each as defined above,

[0062] are reacted with phosphorus compounds of the formula (VIII)

[0063] in which

[0064] L, R⁴ and R⁵ are each as defined above and

[0065] Hal represents halogen (in particular chlorine or bromine),

[0066] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0067] (G) that compounds of the formula (I-f) shown above in which E,A, B, W, X, Y and Z are each as defined above are obtained whencompounds of the formula (I-a) in which A, B, W, X, Y and Z are each asdefined above,

[0068] are reacted with metal compounds or amines of the formulae (IX)or (X)

[0069] in which

[0070] Me represents a mono- or divalent metal (preferably an alkalimetal or alkaline earth metal such as lithium, sodium, potassium,magnesium or calcium),

[0071] t represents the number 1 or 2 and

[0072] R⁹, R¹⁰, R¹¹ independently of one another each represent hydrogenor alkyl (preferably C₁-C₈-alkyl),

[0073] if appropriate in the presence of a diluent;

[0074] (H) that compounds of the formula (I-g) shown above in which L,R⁶, R⁷, A, B, W, X, Y and Z are each as defined above are obtained whencompounds of the formula (I-a) shown above in which A, B, W, X, Y and Zare each as defined above,

[0075] α) are reacted with isocyanates or isothiocyanates of the formula(XI)

R⁶—N═C═L  (XI)

[0076] in which

[0077] R⁶ and L are each as defined above,

[0078] if appropriate in the presence of a diluent and if appropriate inthe presence of a catalyst, or

[0079] β) are reacted with carbamoyl chlorides or thiocarbamoylchlorides of the formula (XII)

[0080] in which

[0081] L, R⁶ and R⁷ are each as defined above,

[0082] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

[0083] Furthermore, it has been found that the novel compounds of theformula (I) have very good activity as pesticides, preferably asinsecticides and as acaricides, and as herbicides, and that they areadditionally frequently very well tolerated by plants, in particular bycrop plants.

[0084] The formula (I) provides a general definition of the compoundsaccording to the invention. Preferred substituents and/or ranges of theradicals listed in the formula mentioned hereinabove and hereinbelow areillustrated below:

[0085] W preferably represents hydrogen, nitro, cyano, halogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl or C₁-C₄-halogenoalkoxy.

[0086] X preferably represents halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, C₂-C₆-halogenoalkenyloxy, cyano, nitro orrepresents phenyl, phenoxy, phenylthio, phenyl-C₁-C₄-alkoxy orphenyl-C₁-C₄-alkylthio, each of which is optionally substituted byhalogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, nitro or cyano.

[0087] Y preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

[0088] Z preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, hydroxyl,cyano, nitro or represents phenoxy, phenylthio, thiazolyloxy,pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-C₁-C₄-alkyloxy orphenyl-C₁-C₄-alkylthio, each of which is optionally substituted byhalogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenalkoxy, nitro or cyano.

[0089] A preferably represents C₁-C₆-alkyl or represents phenyl which isoptionally substituted by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, nitro orcyano.

[0090] B preferably represents hydrogen or C₁-C₆-alkyl.

[0091] G preferably represents hydrogen (a) or represents one of theradicals

[0092]

[0093] in which

[0094] E represents a metal ion equivalent or an ammonium ion,

[0095] L represents oxygen or sulphur and

[0096] M represents oxygen or sulphur.

[0097] R¹ preferably represents C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl, each of which is optionally substitutedby halogen or cyano, or represents C₃-C₈-cycloalkyl in which optionallyone or two not directly adjacent methylene groups are replaced by oxygenand/or sulphur and which is optionally substituted by halogen,C₁-C₆-alkyl or C₁-C₆-alkoxy,

[0098] represents phenyl which is optionally substituted by halogen,cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl,C₁-C₆-halogenoalkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl,

[0099] represents phenyl-C₁-C₆-alkyl which is optionally substituted byhalogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl orC₁-C₆-halogenoalkoxy,

[0100] represents 5- or 6-membered hetaryl having one or two heteroatoms selected from the group consisting of oxygen, sulphur and nitrogen(for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl orthienyl) which is optionally substituted by halogen or C₁-C₆-alkyl,

[0101] represents phenoxy-C₁-C₆-alkyl which is optionally substituted byhalogen or C₁-C₆-alkyl or

[0102] represents 5- or 6-membered hetaryloxy-C₁-C₆-alkyl having one ortwo hetero atoms selected from the group consisting of oxygen, sulphurand nitrogen (for example pyridyloxy-C₁-C₆-alkyl,pyrimidyloxy-C₁-C₆-alkyl or thiazolyloxy-C₁-C₆-alkyl) which isoptionally substituted by halogen, amino or C₁-C₆-alkyl.

[0103] R² preferably represents C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl or poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, each of whichis optionally substituted by halogen or cyano,

[0104] represents C₃-C₈-cycloalkyl which is optionally substituted byhalogen, C₁-C₆-alkyl or C₁-C₆-alkoxy or

[0105] represents phenyl or benzyl, each of which is optionallysubstituted by halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-halogenoalkyl or C₁-C₆-halogenoalkoxy.

[0106] R³ preferably represents C₁-C₈-alkyl which is optionallysubstituted by halogen or represents phenyl or benzyl, each of which isoptionally substituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

[0107] R⁴ and R⁵ independently of one another each preferably representC₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino,C₁-C₈-alkylthio or C₃-C₈-alkenylthio, each of which is optionallysubstituted by halogen, or represents phenyl, phenoxy or phenylthio,each of which is optionally substituted by halogen, nitro, cyano,C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy, C₁-C₄-alkylthio,C₁-C₄-halogenoalkylthio, C₁-C₄-alkyl or C₁-C₄-halogenoalkyl.

[0108] R⁶ and R⁷ independently of one another each preferably representhydrogen, represent C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy,C₃-C₈-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl, each of which is optionallysubstituted by halogen or cyano or represents phenyl or benzyl, each ofwhich is optionally substituted by halogen, C₁-C₈-alkyl,C₁-C₈-halogenoalkyl or C₁-C₈-alkoxy, or together represent aC₃-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur and which is optionally substituted byC₁-C₆-alkyl.

[0109] W particularly preferably represents hydrogen, nitro, cyano,fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl or C₁-C₂-halogenoalkoxy.

[0110] X particularly preferably represents fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, C₂-C₄-halogenoalkenyloxy, cyano, nitro orrepresents phenyl or benzyloxy, each of which is optionally substitutedby fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyano.

[0111] Y particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro.

[0112] Z particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, hydroxyl, cyano, nitro or represents phenoxy orbenzyloxy, each of which is optionally substituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano.

[0113] A particularly preferably represents C₁-C₄-alkyl or representsphenyl.

[0114] B particularly preferably represents hydrogen, methyl or ethyl.

[0115] G particularly preferably represents hydrogen (a) or representsone of the radicals

[0116] (in particular represents one of the radicals (a), (b) or (c)),in which

[0117] E represents a metal ion equivalent or an ammonium ion,

[0118] L represents oxygen or sulphur and

[0119] M represents oxygen or sulphur.

[0120] R¹ particularly preferably represents C₁-C₁₆-alkyl,C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₁-C₆-alkyl, each of which is optionally substitutedby fluorine, chlorine, or represents C₃-C₇-cycloalkyl in whichoptionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur and which is optionally substituted byfluorine, chlorine, C₁-C₅-alkyl or C₁-C₅-alkoxy,

[0121] represents phenyl, which is optionally substituted by fluorine,chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₃-halogenoalkyl, C₁-C₃-halogenoalkoxy, C₁-C₄-alkylthio orC₁-C₄-alkylsulphonyl,

[0122] represents phenyl-C₁-C₄-alkyl which is optionally substituted byfluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₃-halogenoalkyl or C₁-C₃-halogenoalkoxy,

[0123] represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl orthienyl, each of which is optionally substituted by fluorine, chlorine,bromine or C₁-C₄-alkyl,

[0124] represents phenoxy-C₁-C₅-alkyl which is optionally substituted byfluorine, chlorine, bromine or C₁-C₄-alkyl or

[0125] represents pyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkyl orthiazolyloxy-C₁-C₅-alkyl, each of which is optionally substituted byfluorine, chlorine, bromine, amino or C₁-C₄-alkyl.

[0126] R² particularly preferably represents C₁-C₆-alkyl,C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₂-C₆-alkyl, each of which is optionally substitutedby fluorine or chlorine,

[0127] represents C₃-C₇-cycloalkyl which is optionally substituted byfluorine, chlorine, C₁-C₄-alkyl or C₁-C₄-alkoxy or

[0128] represents phenyl or benzyl, each of which is optionallysubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl,C₁-C₃-alkoxy, C₁-C₃-halogenoalkyl or C₁-C₃-halogenoalkoxy.

[0129] R³ particularly preferably represents C₁-C₆-alkyl which isoptionally substituted by fluorine or chlorine or represents phenyl orbenzyl, each of which is optionally substituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkoxy,C₁-C₂-halogenoalkyl, cyano or nitro.

[0130] R⁴ and R⁵ independently of one another particularly preferablyrepresent C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio or C₃-C₄-alkenylthio, each ofwhich is optionally substituted by fluorine or chlorine, or representphenyl, phenoxy or phenylthio, each of which is optionally substitutedby fluorine, chlorine, bromine, nitro, cyano, C₁-C₃-alkoxy,C₁-C₃-halogenoalkoxy, C₁-C₃ -alkylthio, C₁-C₃-halogenoalkylthio,C₁-C₃-alkyl or C₁-C₃-halogenoalkyl.

[0131] R⁶ and R⁷ independently of one another particularly preferablyrepresent hydrogen, represent C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl, each of whichis optionally substituted by fluorine or chlorine, or represent phenylor benzyl, each of which is optionally substituted by fluorine,chlorine, bromine, C₁-C₅-halogenoalkyl, C₁-C₅-alkyl or C₁-C₅-alkoxy, ortogether represent a C₃-C₆-alkylene radical in which optionally onemethylene group is replaced by oxygen or sulphur and which is optionallysubstituted by C₁-C₄-alkyl.

[0132] In the radical definitions referred to as being (particularly)preferred, halogen in combination with other radicals (for example inhalogenoalkyl, halogenoalkoxy or halogenoalkenyloxy) in particularrepresents fluorine, chlorine and bromine, specifically fluorine andchlorine.

[0133] W very particularly preferably represents hydrogen, nitro, cyano,fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, methoxy, ethoxy, n-propoxy, isopropoxy,trifluoromethyl, difluoromethoxy or trifluoromethoxy.

[0134] X very particularly preferably represents fluorine, chlorine,bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, methoxy,ethoxy, n-propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano or nitro.

[0135] Y very particularly preferably. represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl,isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isoproppxy,trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro.

[0136] Z very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl,isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy,trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro.

[0137] A very particularly preferably represents methyl or ethyl.

[0138] B very particularly preferably represents hydrogen or methyl.

[0139] G very particularly preferably represents hydrogen (a) orrepresents one of the radicals

[0140] (in particular represents one of the radicals (a), (b) or (c)),

[0141] in which

[0142] E represents a metal ion equivalent or an ammonium ion,

[0143] L represents oxygen or sulphur and

[0144] M represents oxygen or sulphur.

[0145] R¹ very particularly preferably represents C₁-C₁₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl, C₁-C₄-alkylthio-C₁-C₆-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl, each of which is optionally substitutedby fluorine or chlorine, or represents C₃-C₆-cycloalkyl in whichoptionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur and which is optionally substituted byfluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,tert-butyl, methoxy, ethoxy, n-propoxy or isopropoxy,

[0146] represents phenyl which is optionally substituted by fluorine,chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl,methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylthio,ethylthio, methylsulphonyl or ethylsulphonyl,

[0147] represents benzyl which is optionally substituted by fluorine,chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy,trifluoromethyl or trifluoromethoxy,

[0148] represents furanyl, thienyl or pyridyl, each of which isoptionally substituted by fluorine, chlorine, bromine, methyl or ethyl,

[0149] represents phenoxy-C₁-C₄-alkyl which is optionally substituted byfluorine, chlorine, methyl or ethyl or

[0150] represents pyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl orthiazolyloxy-C₁-C₄-alkyl, each of which is optionally substituted byfluorine, chlorine, amino, methyl or ethyl.

[0151] R² very particularly preferably represents C₁-C₁₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₄-alkoxy-C₂-C₆-alkyl, each of which is optionally substitutedby fluorine or chlorine,

[0152] represents C₃-C₆-cycloalkyl which is optionally substituted byfluorine, chlorine, methyl, ethyl, n-propyl, isopropyl or methoxy,

[0153] or represents phenyl or benzyl, each of which is optionallysubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl,n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy.

[0154] R³ very particularly preferably represents methyl, ethyl,n-propyl, isopropyl, n-butyl, tert-butyl, each of which is optionallysubstituted by fluorine or chlorine, or represents phenyl or benzyl,each of which is optionally substituted by fluorine, chlorine, bromine,methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro.

[0155] R⁴ and R⁵ independently of one another each very particularlypreferably represent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino or C₁-C₄-alkylthio, each of which is optionallysubstituted by fluorine or chlorine, or represent phenyl, phenoxy orphenylthio, each of which is optionally substituted by fluorine,chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl ortrifluoromethoxy.

[0156] R⁶ and R⁷ independently of one another each very particularlypreferably represent hydrogen, represent C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which isoptionally substituted by fluorine or chlorine, or represent phenyl orbenzyl, each of which is optionally substituted by fluorine, chlorine,bromine, methyl, methoxy or trifluoromethyl, or together represent aC₅-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur and which is optionally substituted bymethyl or ethyl.

[0157] Especially preferred are compounds of the formula (1), in which Arepresents CH₃ and B represents hydrogen, in particular in combinationwith the very particularly preferred radicals mentioned for G.

[0158] The abovementioned general or preferred definitions of radicalsor illustrations can be combined with each other as desired, that is tosay combinations between the ranges and preferred ranges in question arealso possible. They apply both to the end products and, correspondingly,to the starting materials and intermediates.

[0159] Preference according to the invention is given to those compoundsof the formula (I) which contain a combination of the definitions givenabove as being preferred (preferable).

[0160] Particular preference according to the invention is given tothose compounds of the formula (I) which contain a combination of thedefinitions given above as being particularly preferred.

[0161] Very particular preference according to the invention is given tothose compounds of the formula (I) which contain a combination of thedefinitions given above as being very particularly preferred.

[0162] Saturated or unsaturated hydrocarbon radicals such as alkyl oralkenyl may be, also in connection with hetero atoms such as, forexample, in alkoxy, in each case straight-chain or branched as far asthis is possible.

[0163] Optionally substituted radicals may be mono- or polysubstituted,it being possible for the substituents in the case of polysubstitutionsto be identical or different.

[0164] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-a) may be mentionedspecifically: TABLE 1 A = CH₃; B = H (I-a)

X W Y Z Br H Cl H Cl H Br H Cl H Cl H Cl H F H F H Cl H Cl H OCH₃ H Cl HCH₃ H OCH₃ H Cl H OCH₃ H OCH₃ H CH₃ H Cl H CH₃ H F H CH₃ H OCH₃ H CH₃ Ht-C₄H₉ H CH₃ H CH₃ H Cl Cl H H Cl F H H Cl OCH₃ H H Cl CH₃ H H Cl OC₂H₅H H OCH₃ OCH₃ H H CH₃ CH₃ H H Br CH₃ Br H Cl Cl CH₃ H CH₃ Br CH₃ H CH₃Cl CH₃ H CH₃ OCHF₂ CH₃ H CH₃ OCH₂CF₃ CH₃ H CH₃ OC₂H₅ CH₃ H CH₃ OCH₃ CH₃H CH₃ CH₃ CH₃ H Br Br CH₃ H Cl Cl CH₃ H C₂H₅ C₂H₅ Br H CH₃ CH₃ Br H CH₃CH₃ OCH₃ H Br Cl CH₃ H Br CH₃ Cl H Cl CH₃ Br H C₂H₅ Br CH₃ H CH₃ O-C₃H₇CH₃ H CH₃ CH₃ Cl H Cl H Cl Cl CH₃ H CH₃ CH₃ CH₃ H Cl CH₃ Br H Cl CH₃ BrH CH₃ CH₃ Cl H Br CH₃ Cl H Cl CH₃ CH₃ H Br CH₃ Cl H Cl F Cl H CH₃ Cl CH₃H H H Cl H H H Br H H H CF₃ H H H OCH₃ H H H CH₃ CH₃ CH₃ CH₃ CH₃ H CH₃CH₃ CH₃ CH₃ H CH₃ CH₃ CH₃ CH₃ F CH₃ CH₃ CH₃ Cl CH₃ CH₃ CH₃ Br CH₃ CH₃ HCl CH₃ CH₃ H Br Cl Cl H Br

[0165] Using according to process (A)N-[(4-chloro-2,6-dimethyl)-phenylacetyl]-4-amino-4-carboxyethyl-2-methyl-tetrahydropyranas starting material, the course of the process according to theinvention can be represented by the following equation:

[0166] Using according to process (Bα)3-[(2-chloro-4-methyl)-phenyl]-5,5-[(2-ethyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

[0167] Using according to process (B) (variant β)3-[(2,4-dichloro)-phenyl]-5,5-[(2-methyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following equation:

[0168] Using according to process (C)8-[(2,4-dichloro)-phenyl]-5,5-[(2-methyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

[0169] Using according to process. (D)3-[(2,6-dibromo-4-methyl)-phenyl]-5,5-[(2-ethyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

[0170] Using according to process (E)2-[(2,4,6-trimethyl)-phenyl]-5,5-[(2-methyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following equation:

[0171] Using according to process (F)2-[(4-bromo-2-chloro-6methyl)-phenyl]-4-hydroxy-5,5-[(2-methyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand (2,2,2-trifluoroethyl) methanethio-phosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing equation:

[0172] Using according to process (G)3-[(2,4-dichloro)-6-methylphenyl]-5,5-[(2-ethyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the following equation:

[0173] Using according to process (H) (variant a)3-[(2-chloro-4-bromo-5-methyl)-phenyl]-4-hydroxy-5,5-[(2-methyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the following equation:

[0174] Using according to process (H) (variant β)3-[(2-chloro-4,6-dimethyl)-phenyl]-5,5[(2-methyl)-ethyleneoxyethyl]-pyrrolidine-2,4-dioneand dimethylcarbamidoyl chloride as starting materials, the course ofthe reaction can be represented by the following equation:

[0175] The compounds of the formula (II) required as starting materialsin the process (A) according to the invention

[0176] in which

[0177] A, B, W, X, Y, Z and R⁸ are each as defined above, are novel.

[0178] The acylamino acid esters of the formula (II) are obtained, forexample, when amino acid derivatives of the formula (XIII)

[0179] in which

[0180] A, B and R⁸ are each as defined above,

[0181] are acylated with substituted phenylacetyl halides of the formula(XIV)

[0182] in which

[0183] W, X, Y and Z are each as defined above and

[0184] Hal represents chlorine or bromine,

[0185] (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem.6, 341-5, 1968)

[0186] or when acylamino acids of the formula (XV)

[0187] in which

[0188] A, B, W, X, Y and Z are each as defined above,

[0189] are esterified (Chem. Ind. (London) 1568 (1968)).

[0190] The compounds of the formula (XV)

[0191] in which

[0192] A, B, W, X, Y and Z are each as defined above,

[0193] are novel.

[0194] The compounds of the formula (XV) are obtained, for example, when4-amino-tetrahydropyran-4-carboxylic acids of the formula (XVI)

[0195] in which

[0196] A and B are each as defined above

[0197] are acylated according to Schotten-Baumann (Organikum, VEBDeutscher Verlag der Wissenschaften, Berlin 1977, P. 505) withsubstituted phenylacetyl halides of the formula (XIV)

[0198] in which

[0199] W, X, Y and Z are each as defined above and

[0200] Hal represents chlorine or bromine.

[0201] Some of the compounds of the formula (XIV) are novel and can beprepared by known processes (cf., for example, DE-196 49 665).

[0202] The compounds of the formula (XIV) are obtained, for example, byreacting substituted phenylacetic acids of the formula (XVII)

[0203] in which

[0204] W, X, Y and Z are each as defined above

[0205] with halogenating agents (for example thionyl chloride, thionylbromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorustribromide or phosphorus pentachloride), if appropriate in the presenceof a diluent (for example optionally chlorinated aliphatic or aromatichydrocarbons such as toluene or methylene chloride) at temperatures offrom −20° C. to 150° C., preferably of from −10° C. to 100° C.

[0206] Some of the compounds of the formula (XVII) are novel, they canbe prepared by processes known from the literature (Organikum 15thedition, p. 533, VEB Deutscher Verlag der Wissenschaften, Berlin 1977,cf., for example, DE-196 49 665).

[0207] The compounds of the formula (XVII) are obtained, for example, byhydrolysing substituted phenylacetic esters of the formula (XVIII)

[0208] in which

[0209] W, X, Y, Z and R⁸ are each as defined above

[0210] in the presence of an acid (for example an inorganic acid such ashydrochloric acid) or a base (for example an alkali metal hydroxide suchas sodium hydroxide or potassium hydroxide) and, if appropriate, adiluent (for example an aqueous alcohol such as methanol or ethanol) attemperatures between 0° C. and 150° C., preferably between 20° C. and100° C.

[0211] Some of the compounds of the formula (XVIII) are novel, they canbe prepared by processes known in principle.

[0212] The compounds of the formula (XVIII) are obtained, for example,by reacting substituted 1,1,1-trichloro-2-phenylethanes of the formula(XIX)

[0213] in which

[0214] W, X, Y and Z are each as defined above

[0215] initially with alkoxides (for example alkali metal alkoxides suchas sodium methoxide or sodium ethoxide) in the presence of a diluent(for example of the alcohol derived from the alkoxide) at temperaturesbetween 0° C. and 150° C., preferably between 20° C. and 120° C., andsubsequently reacting with an acid (preferably an inorganic acid, suchas, for example, sulphuric acid) at temperatures between −20° C. and150° C. preferably between 0° C. and 100° C. (cf. DE-3 314 249).

[0216] Some of the compounds of the formula (XIX) are novel, they can beprepared by processes known in principle.

[0217] The compounds of the formula (XIX) are obtained, for example,when anilines of the formula (XX)

[0218] in which

[0219] W, X, Y and Z are each as defined above

[0220] are reacted in the presence of alkyl nitrite of the formula (XXI)

R¹³—ONO  (XXI)

[0221] in which

[0222] R¹³ represents alkyl, preferably C₁-C₆-alkyl,

[0223] in the presence of copper(II) chloride and if appropriate in thepresence of a diluent (for example an aliphatic nitrile such asacetonitrile) at a temperature of from −20° C. to 80° C., preferably offrom 0° C. to 60° C., with vinylidene chloride (CH₂═CCl₂).

[0224] Some of the compounds of the formula (XX) are known. They can beprepared by processes known from the literature, for example byreduction of the corresponding nitro compounds or halogenation of theanilines or acetanilides and subsequent recleavage.

[0225] The compounds of the formula (XXI) are known compounds of organicchemistry. Copper(II) chloride and vinylidene chloride have been knownfor a long time and are commercially available.

[0226] The substituted cyclic aminocarboxylic acids of the formula (XVI)are generally obtainable by the Bucherer-Bergs synthesis or by theStrecker synthesis and are in each case obtained in these syntheses indifferent isomer forms. Thus, under the conditions of the Bucherer-Bergssynthesis, the isomers (for simplicity called β below), in which theradicals R and the carboxyl group are equatorial are predominantlyobtained, while under the conditions of the Strecker synthesis theisomers (for simplicity called α below) in which the amino group and theradicals R are equatorial are predominantly obtained.

[0227] The compounds of the formula (XIII) and (XVI) are novel. They canbe prepared by known processes (see, for example, Compagnon, Ann. Chim.(Paris) [14] 5, p. 11-22, 23-27 (1970), L. Munday, J. Chem. Soc. 4372(1961); J. T. Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975)).

[0228] Furthermore, the starting materials of the formula (II)

[0229] in which

[0230] A, B, W, X, Y, Z and R⁸ are each as defined above,

[0231] used in the above process (A) can be prepared when aminonitrilesof the formula (XXII)

[0232] in which

[0233] A and B are each as defined above,

[0234] are reacted with substituted phenylacetyl halides of the formula(XIV)

[0235] in which

[0236] W, X, Y, Z and Hal are each as defined above

[0237] to give compounds of the formula (XXIII)

[0238] in which

[0239] A, B, W, X, Y and Z are each as defined above

[0240] and these are subsequently subjected to acid alcoholysis.

[0241] The compounds of the formula (XXIII) are also novel. Thecompounds of the formula (XXII) are also novel.

[0242] The acyl halides of the formula (III), carboxylic anhydrides ofthe formula (IV), chloroformic esters or chloroformic thioesters of theformula (V), chloromonothioformic esters or chlorodithioformic esters ofthe formula (VI), sulphonyl chlorides of the formula (VII), phosphoruscompounds of the formula (VIII) and metal hydroxides, metal alkoxides oramines of the formula (IX) and (X) and isocyanates of the formula (XI)and carbamoyl chlorides of the formula (XII) furthermore required asstarting materials for carrying out the processes (B), (C), (D), (E),(F), (G) and (H) according to the invention are generally knowncompounds of organic or inorganic chemistry.

[0243] The compounds of the formulae (XIV), (XVII), (XVIII), (XIX) and(XX) are furthermore known from the patent applications cited at theoutset and/or can be prepared by the methods given therein (cf. alsoDE-196 49 665 and the Applicant's German Patent Application having filereference 19613171.5 dated 02.04.1996, which has not yet been laidopen).

[0244] The process (A) is characterized in that compounds of the formula(II), in which A, B, W, X, Y, Z and R⁸ are each as defmed above aresubjected to an intramolecular condensation in the presence of a diluentand in the presence of a base.

[0245] Suitable diluents for use in the process (A) according to theinvention are all organic solvents which are inert towards thereactants. Preference is given to using hydrocarbons, such as tolueneand xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran,dioxane, glycol dimethyl ether and diglycol dimethyl ether, moreoverpolar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone, and also alcohols such asmethanol, ethanol, propanol, isopropanol, butanol, isobutanol andtert-butanol.

[0246] Suitable bases (deprotonating agents) for use in the practice ofthe process (A) according to the invention are all customary protonacceptors. Preference is given to using alkali metal and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which may also be used in thepresence of phase transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(═methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(═tris-(methoxyethoxyethyl)-amine). It is also possible to use alkalimetals such as sodium or potassium.

[0247] Furthermore, it is possible to use alkali metal and alkalineearth metal amides and hydrides, such as sodium amide, sodium hydrideand calcium hydride, and moreover also alkali metal alkoxides, such assodium methoxide, sodium ethoxide and potassium tert-butoxide.

[0248] When carrying out the process (A) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −75° C. and200° C., preferably between −50° C. and 150° C.

[0249] The process (A) according to the invention is generally carriedout under atmospheric pressure.

[0250] When carrying out the process (A) according to the invention, thereaction component of the formula (II) and the deprotonating base aregenerally employed in equimolar to about doubly-equimolar amounts.However, it is also possible to use one component or the other in arelatively large excess (up to 3 mol).

[0251] The process (B_(α)) is characterized in that compounds of theformula (I-a) are reacted with carbonyl halides of the formula (III), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

[0252] Suitable diluents for use in the process (B_(α)) according to theinvention are all solvents which are inert towards the acyl halides.Preference is given to using hydrocarbons, such as benzine, benzene,toluene, xylene and tetralin, furthermore halogenated hydrocarbons, suchas methylene chloride, chloroform, carbon tetrachloride, chlorobenzeneand o-dichlorobenzene, furthermore ketones, such as acetone and methylisopropyl ketone, additionally ethers, such as diethyl ether,tetrahydrofuran and dioxane, furthermore, carboxylic esters, such asethyl acetate, and also strongly polar solvents, such asdimethylformamide, dimethyl sulphoxide and sulpholane. The hydrolyticstability of the acyl halide permitting, the reaction can also becarried out in the presence of water.

[0253] Suitable acid binders for the reaction according to the process(B_(α)) according to the invention are all customary acid acceptors.Preference is given to using tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, and also alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate and also alkali metal hydroxides such as sodium hydroxide andpotassium hydroxide.

[0254] The reaction temperature of the process (B_(α)) according to theinvention can be varied within a relatively wide range. In general, thereaction is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

[0255] When carrying out the process (B_(α)) according to the invention,the starting materials of the formula (I-a) and the carbonyl halide ofthe formula (III) are generally each employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (up to 5 mol) of the carbonyl halide. Work-up is carriedout by customary methods.

[0256] The process (Bβ) is characterized in that compounds of theformula (I-a) are reacted with carboxylic anydrides of the formula (IV),if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

[0257] Suitable diluents for use in the process (Bβ) according to theinvention are preferably those diluents which are also preferred whenacyl halides are used. Additionally, a carboxylic anhydride employed inexcess can also simultaneously act as diluent.

[0258] The acid binders which are added in the process (Bβ), ifappropriate, are preferably those acid binders which are also preferredwhen acyl halides are used.

[0259] The reaction temperature in the process (Bβ) according to theinvention can be varied within a relatively wide range. In general, thereaction is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

[0260] When carrying out the process (Bβ) according to the invention,the starting materials of the formula (I-a) and the carboxylic anhydrideof the formula (IV) are generally each employed in approximatelyequivalent amounts. However, it is also possible to employ a relativelylarge excess (up to 5 mol) of the carboxylic anhydride. Work-up iscarried out by customary methods.

[0261] In general, diluent and excess carboxylic anhydride and also thecarboxylic acid formed are removed by distillation or by washing with anorganic solvent or with water.

[0262] The process (C) is characterized in that compounds of the formula(I-a) are reacted with chloroformic esters or chloroformic thiol estersof the formula (V), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

[0263] Acid binders which are suitable for the process (C) according tothe invention are all customary acid acceptors. Preference is given tousing tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN,Hünig base and N,N-dimethyl-aniline, furthermore alkaline earth metaloxides, such as magnesium oxide and calcium oxide, moreover alkali metaland alkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal hydroxides suchas sodium hydroxide and potassium hydroxide.

[0264] Suitable diluents for use in the process (C) according to theinvention are all solvents which are inert towards the chloroformicesters or chloroformic thiol esters. Preference is given to usinghydrocarbons, such as benzine, benzene, toluene, xylene and tetralin,furthermore, halogenated hydrocarbons, such as methylene chloride,chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene,furthermore ketones, such as acetone and methyl isopropyl ketone,moreover ethers, such as diethyl ether, tetrahydrofuran and dioxane,furthermore carboxylic esters, such as ethyl acetate, additionallynitriles such as acetonitrile and also strongly polar solvents, such asdimethylformamide, dimethyl sulphoxide and sulpholane.

[0265] When carrying out the process (C) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction temperature is between −20° C. and +100° C.,preferably between 0° C. and 50° C.

[0266] The process (C) according to the invention is generally carriedout under atmospheric pressure.

[0267] When carrying out the process (C) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thiol ester of the formula (VII) are generallyeach employed in approximately equivalent amounts. However, it is alsopossible to employ one component or the other in a relatively largeexcess (up to 2 mol). Work-up is carried out by customary methods. Ingeneral, precipitated salts are removed and the reaction mixture whichremains is concentrated by removing the diluent under reduced pressure.

[0268] The process (D) according to the invention is characterized inthat compounds of the formula (I-a) are reacted with compounds of theformula (VI) in the presence of a diluent and, if appropriate, in thepresence of an acid binder.

[0269] In the preparation process (D), approximately 1 mol ofchloromonothioformic ester or chlorodithioformic ester of the formula(VI) per mole of starting material of the formula (I-a) is reacted at 0to 120° C., preferably at 20 to 60° C.

[0270] Diluents which may be added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides, andalso halogenoalkanes.

[0271] Preference is given to using dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, ethyl acetate or methylene chloride.

[0272] If, in a preferred embodiment, the enolate salt of the compoundsof the formula (I-a) is prepared by addition of strong deprotonatingagents such as, for example, sodium hydride or potassium tert-butoxide,the addition of acid binders can be dispensed with.

[0273] Suitable bases for use in the process (D) are all customaryproton acceptors. Preference is given to using alkali metal hydrides,alkali metal alkoxides, alkali metal or alkaline earth metal carbonatesor bicarbonates or nitrogen bases. Examples include sodium hydride,sodium methoxide, sodium hydroxide, calcium hydroxide, potassiumcarbonate, sodium bicarbonate, triethylarnine, dibenzylamine,diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO),diazabicyclononene (DBN) and diazabicycloundecene (DBU).

[0274] The reaction can be carried out under atmospheric pressure orunder elevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

[0275] The process (E) according to the invention is characterized inthat compounds of the formula (I-a) are in each case reacted withsulphonyl chlorides of the formula (VII), if appropriate in the presenceof a diluent and if appropriate in the presence of an acid binder.

[0276] In the preparation process (E), approximately 1 mol of sulphonylchloride of the formula (IX) per moleof starting material of the formula(I-a) is reacted at −20 to 150° C., preferably at 0 to 70° C.

[0277] The process (E) is preferably carried out in the presence of adiluent.

[0278] Suitable diluents are all inert polar organic solvents such asethers, amides, ketones, carboxylic esters, nitrites, sulphones,sulphoxides or halogenated hydrocarbons such as methylene chloride.

[0279] Preference is given to using dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, ethyl acetate, methylene chloride.

[0280] If, in a preferred embodiment, the enolate salt of the compoundsof the formula (I-a) is prepared by addition of strong deprotonatingagents (such as, for example, sodium hydride or potassiumtert-butoxide), the addition of acid binders can be dispensed with.

[0281] If acid binders are used, then customary inorganic or organicbases are suitable, examples being sodium hydroxide, sodium carbonate,potassium carbonate, pyridine and triethylamine.

[0282] The reaction can be carried out under atmospheric pressure orunder elevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

[0283] The process (F) according to the invention is characterized inthat compounds of the formula (I-a) are in each case reacted withphosphorus compounds of the formula (VIII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

[0284] In the preparation process (F), 1 to 2, preferably 1 to 1.3, molof the phosphorus compound of the formula (VIII) are reacted per mole ofthe compounds of the formula (I-a) at temperatures between −40° C. and150° C., preferably between −10 and 110° C., in order to obtaincompounds of the formula (I-e).

[0285] The process (F) is preferably carried out in the presence of adiluent.

[0286] Suitable diluents are all inert, polar organic solvents such asethers, carboxylic esters, halogenated hydrocarbons, ketones, amides,nitrites, sulphones, sulphoxides, etc.

[0287] Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

[0288] Acid binders which are added, if appropriate, are customaryinorganic or organic bases, such as hydroxides, carbonates or amines.Examples include sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylarnine.

[0289] The reaction can be carried out under atmospheric pressure orunder elevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out according to customary methods oforganic chemistry. The end products are preferably purified bycrystallization, chromatographic purification or by so-called “incipientdistillation”, i.e. removal of the volatile components under reducedpressure.

[0290] The process (G) is characterized in that compounds of the formula(I-a) are in each case reacted with metal hydroxides or metal alkoxidesof the formula (IX) or amines of the formula (X), if appropriate in thepresence of a diluent.

[0291] Diluents which are preferred for use in the process (G) accordingto the invention are ethers such as tetrahydrofuran, dioxane, diethylether, or else alcohols such as methanol, ethanol, isopropanol, but alsowater. The process (G) according to the invention is generally carriedout under atmospheric pressure. The reaction temperature is generallybetween −20° C. and 100° C., preferably between 0° C. and 50° C.

[0292] The process (H) according to the invention is characterized inthat compounds of the formula (I-a) are in each case reacted with (Hα)compounds of the formula (XI), if appropriate in the presence of adiluent and if appropriate in the presence of a catalyst, or (Hβ) withcompounds of the formula (XII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

[0293] In the preparation process (Hα), approximately 1 mol ofisocyanate of the formula (XI) is reacted per mole of starting materialof the formula (I-a) at 0 to 100° C., preferably at 20 to 50° C.

[0294] The process (Hα) is preferably carried out in the presence of adiluent.

[0295] Suitable diluents are all inert organic solvents, such asaromatic hydrocarbons, halogenated hydrocarbons, ethers, amides,nitrites, sulphones or sulphoxides.

[0296] If appropriate, catalysts may be added to accelerate thereaction. Catalysts which can be employed very advantageously areorganotin compounds, such as, for example, dibutyltin dilaurate.

[0297] The process is preferably carried out under atmospheric pressure.

[0298] In the preparation process (Hβ), approximately 1 mol of carbamoylchloride of the formula (XIII) is reacted per mole of starting materialof the formula (I-a) at 0 to 150° C., preferably at 20 to 70° C.

[0299] Diluents which may be added, if appropriate, are all inert polarorganic solvents such as ethers, carboxylic esters, nitriles, ketones,amides, sulphones, sulphoxides or halogenated hydrocarbons.

[0300] Preference is given to using dimethyl sulphoxide,tetrahydrofuran, dimethylformamide or methylene chloride.

[0301] If, in a preferred embodiment, the enolate salt of the compoundsof the formula (I-a) is prepared by addition of strong deprotonatingagents (such as, for example, sodium hydride or potassiumtert-butoxide), the addition of acid binders can be dispensed with.

[0302] If acid binders are employed, then customary inorganic or organicbases are suitable, examples including sodium hydroxide, sodiumcarbonate, potassium carbonate, triethylamine or pyridine.

[0303] The reaction can be carried out under atmospheric pressure orunder elevated pressure and is preferably carried out under atmosphericpressure. Work-up is carried out by customary methods.

[0304] The active compounds are suitable for controlling animal pests,preferably arthropods and nematodes, in particular insects andarachnids, which are encountered in agriculture, in forests, in theprotection of stored products and of materials, and in the hygienefield. They are active against normally sensitive and resistant speciesand against all or some stages of development. The abovementioned pestsinclude:

[0305] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0306] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0307] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spec.

[0308] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0309] From the order of the Thysanura, for example, Lepisma saccharina.

[0310] From the order of the Collembola, for example, Onychiurusarmatus.

[0311] From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

[0312] From the order of the Dermaptera, for example, Forficulaauricularia.

[0313] From the order of the Isoptera, for example, Reticulitermes spp..

[0314] From the order of the Anoplura, for example, Phylloxeravastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp.and Linognathus spp.

[0315] From the order of the Mallophaga, for example, Trichodectes spp.and Damalinea spp.

[0316] From the order of the Thysanoptera, for example, Frankliniellaoccidentalis, Hercinothrips femoralis, Thrips palmi, and Thrips tabaci.

[0317] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0318] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzusspp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelisbilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae,Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii,Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

[0319] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella. Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofinannophila pseudospretella,Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysiaambiguella, Homona magnanima and Tortrix viridana.

[0320] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelidesobtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsadecemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodeschrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilussurinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus,Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica,Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctusspp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbiumpsylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derusspp., Melolontha melolontha, Amphimallon soisti tialis and Costelytrazealandica.

[0321] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0322] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Liriomyza spp., Stomoxys spp.,Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibiohortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitiscapitata, Dacus oleae and Tipula paludosa.

[0323] From the order of the Siphonaptera, for example, Xenopsyllacheopis and Ceratophyllus spp.

[0324] From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

[0325] From the order of the Acarina, for example, Acarus siro, Argasspp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis,Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommaspp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp.,Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. andTetranychus spp.

[0326] The active compounds according to the invention have highinsecticidal and acaricidal activity after foliar and soil application.

[0327] They can be employed particularly successfully against insectswhich are harmful to plants, such as, for example, against the larvae ofthe mustard beetle (Phaedon cochleariae), against the larvae of the ricegreen leafhopper (Nephotettix cincticeps) and against the larvae of thegreen peach aphid (Myzus persicae).

[0328] The active compounds according to the invention can furthermorebe used as defoliants, desiccants, haulm killers and, especially, asweed-killers. By weeds, in the broadest sense, there are to beunderstood all plants which grow in locations where they are undesired.Whether the substances according to the invention act as total orselective herbicides depends essentially on the amount used.

[0329] The dosages of the active compounds according to the inventionnecessary for controlling weeds are between 0.001 and 10 kg/ha,preferably between 0.005 and 5 kg/ha.

[0330] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0331] Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, lpomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotola, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

[0332] Dicotyledonous crops of the genera: Gossypium, Glycine, Beta,Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

[0333] Monocotyledonous weeds of the genera: Echinochloa, Setaria,Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium,Bromus, Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria,Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum,Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

[0334] Monocotyledonous crops of the genera: Oryza, Zea, Triticum,Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagusand Allium.

[0335] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0336] The compounds are suitable, depending on the concentration, forthe total controlling of weeds, for example on industrial terrain andrail tracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial cultures, for example afforestations, decorative treeplantings, orchards, vineyards, citrus groves, nut orchards, bananaplantations, coffee plantations, tea plantations, rubber plantations,oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on ornamental and sports lawns and meadow areas and for theselective controlling of weeds in annual cultures.

[0337] The active compounds according to the invention are particularlysuitable for selectively controlling monocotyledonous weeds indicotyledonous crops by the pre- and post-emergence method. For example,they can be employed very successfully for controlling harmful grassesin cotton or sugar beet.

[0338] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusting agents, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and very fine capsules in polymericsubstances.

[0339] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is liquid solventsand/or solid carriers, optionally with the use of surface-active agents,that is emulsifying agents and/or dispersing agents and/or foam-formingagents.

[0340] If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, and also water.

[0341] As solid carriers there are suitable:

[0342] for example, ammonium salts and ground natural minerals, such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates; as solid carriers for granulesthere are suitable: for example, crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite, and alsosynthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; as emulsifying and/or foam-forming agents there are suitable:for example, non-ionic and anionic emulsifiers, such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; as dispersing agents thereare suitable: for example, lignin-sulphite waste liquors andmethylcellulose.

[0343] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latexes, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

[0344] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0345] The formulations in general contain between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%, and additionallypreferably extenders and/or surfactants.

[0346] The active compound according to the invention can be present inits commercially available formulations and in the use forms preparedfrom these formulations as a mixture with other active compounds, suchas insecticides, baits, sterilizing agents, acaricides, nematicides,fungicides, growth-regulating substances or herbicides. The insecticidesinclude, for example, phosphoric acid esters, carbamates, carboxylicacid esters, chlorinated hydrocarbons, phenylureas, substances producedby microorganisms, and the like.

[0347] Particularly favourable mixing partners are, for example, thefollowing:

[0348] Fungicides

[0349] 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2′,6′-dibromo-2methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide;(E)-2-methoxyimino-N-methyl-2(2-phenoxy-phenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

[0350] benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

[0351] calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

[0352] dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

[0353] edifenphos, epoxyconazole, ethirimol, etridiazole,

[0354] fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

[0355] guazatine,

[0356] hexachlorobenzene, hexaconazole, hymexazol,

[0357] imazalil, imibenconazole, iminoctadine, iprobenfos (IBP),iprodione, isoprothiolane,

[0358] kasugamycin, copper preparations such as: copper hydroxide,copper naphthenate, copper oxychloride, copper sulphate, copper oxide,oxine-copper and Bordeaux

[0359] mixture, mancopper, mancozeb, maneb, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metsulfovax, myclobutanil,

[0360] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0361] ofurace, oxadixyl, oxamocarb, oxycarboxin,

[0362] pefurazoate, penconazole, pencycuron, phosdiphen, phthalide,pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz,procymidone, propamocarb, propiconazole, propineb, pyrazophos,pyrifenox, pyrimethanil, pyroquilon,

[0363] quintozene (PCNB),

[0364] sulphur and sulphur preparations,

[0365] tebuconazole, tecloftalam, tecnazene, tetraconazole,thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide,tricyclazole, tridemorph, triflumizole, triforine, triticonazole,

[0366] validamycin A, vinclozolin,

[0367] zineb, ziram

[0368] Bactericides

[0369] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugarnycin, octhilinon, furancarboxylic acid,oxytetracyclin, probenazol, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0370] Insecticides/Acaricides/Nematicides

[0371] abamectin, AC 303 630, acephate, acrinathrin, alanycarb,aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin,azinphos A, azinphos M, azocyclotin,

[0372] Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,beta-cyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxin, butylpyridaben,

[0373] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, CGA 157 419, CGA 184 699, chloethocarb, chlorethoxyfos,chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifosM, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

[0374] deltamethrin, demeton-M, demeton-S, demeton-S-methyl,diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos,dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos,dioxathion, disulfoton,

[0375] edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion,ethofenprox, ethoprophos, etrimphos,

[0376] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad,fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam,flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate,fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,

[0377] HCH, heptenophos, hexaflumuron, hexythiazox,

[0378] imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb,isoxathion, ivermectin,

[0379] lambda-cyhalothrin, lufenuron,

[0380] malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde,methacrifos, methamidophos, methidathion, methiocarb, methomyl,metolcarb, milbemectin, monocrotophos, moxidectin,

[0381] naled, NC 184, NI 25, nitenpyram,

[0382] omethoate, oxamyl, oxydemethon M, oxydeprofos,

[0383] parathion A, parathion M, permethrin, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M,primiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos,prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin,pyrethrum, pyridaben, pyrimidifen, pyriproxifen,

[0384] quinalphos,

[0385] RH 5992,

[0386] salithion, sebufos, silafluofen, sulfotep, sulprofos,

[0387] tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron,tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox,thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin,tralomethrin, triarathen, triazophos, triazuron, trichlorfon,triflumuron, trimethacarb,

[0388] vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

[0389] Herbicides

[0390] for example anilides, such as, for example, diflufenican andpropanil; arylcarboxylic acids such as, for example, dichloropicolinicacid, dicamba and picloram; aryloxyalkanoic acids, such as, for example,2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic acid esters, such as, for example,diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones, such as, for example, chloridazon andnorflurazon; carbamates, such as, for example, chlorpropham,desmedipham, phenmedipham and propham; chloroacetanilides, such as, forexample, alachlor, acetochlor, butachlor, metazachlor, metolachlor,pretilachlor and propachlor; dinitroanilines, such as, for example,oryzalin, pendimethalin and trifluralin; diphenyl ethers, such as, forexample, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen,lactofen and oxyfluorfen; ureas, such as, for example, chlortoluron,diuron, fluometuron, isoproturon, linuron and methabenzthiazuron;hydroxylamines, such as, for example, alloxydim, clethodim, cycloxydim,sethoxydim and traikoxydim; imidazolinones, such as, for example,imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, such as,for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides, suchas, for example, mefenacet; sulfonylureas, such as, for example,amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron,pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron andtribenuron-methyl; thiocarbamates, such as, for example, butylate,cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb,thiobencarb and tri-allate; triazines, such as, for example, atrazine,cyanazine, simazine, simetryn, terbutryn and terbutylazine; triazinones,such as, for example, hexazinone, metamitron and metribuzin; others,such as, for example, aminotriazole, benfuresate, bentazone,cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr,ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben,pyridate, quinchlorac, quinmerac sulphosate and tridiphane.

[0391] The active compound according to the invention can furthermore bepresent in its commercially available formulations and in the use forms,prepared from these formulations, as a mixture with synergists.Synergists are compounds which increase the action of the activecompounds without it being necessary for the synergist added to beactive itself.

[0392] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[0393] The compounds are used in a customary manner appropriate for theuse forms.

[0394] When used against hygiene pests and pests of stored products, theactive compound has outstanding residual action on wood and clay and astability to alkali on limed substrates.

[0395] The active compounds according to the invention have an actionnot only against plant and hygiene pests and pests of stored products,but also in the veterinary medicine sector against animal parasites(ectoparasites), such as hard ticks, soft ticks, mange mites, harvestmites, flies (biting and licking), parasitic fly larvae, lice, hairlice, bird lice and fleas. These parasites include:

[0396] From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[0397] From the order of the Mallophagida and the suborders Amblycerinaand Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

[0398] From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[0399] From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

[0400] From the order of the Heteropterida, for example, Cimex spp.,Triatoma spp., Rhodnius spp. and Panstrongylus spp.

[0401] From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

[0402] From the sub-class of the Acaria (Acarida) and the orders of theMeta- and Mesostigmata, for example, Argas spp., Ornithodorus spp.,Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentorspp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroaspp.

[0403] From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0404] The active compounds of the formula (I) according to theinvention are also suitable for controlling arthropods which. infestagricultural productive livestock such as, for example, cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese and bees, other pets, such as, for example, dogs,cats, cage birds and aquarium fish, and also so-called test animals,such as, for example, hamsters, guinea pigs, rats and mice. Bycontrolling these arthropods, mortality and reductions in productivity(for meat, milk, wool, hides, eggs, honey, etc.) should be diminished,so that more economic and simpler animal husbandry is possible by use ofthe active compounds according to the invention.

[0405] The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boli, the feed-through process and suppositories, by parenteraladministration, such as, for example, by injections (intramuscular,subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasaladministration, by dermal use in the form, for example, of dipping orbathing, spraying, pouring on and spotting on, washing and powdering,and also with the aid of moulded articles containing the activecompound, such as collars, ear marks, tail marks, limb bands, halters,marking devices, etc.

[0406] When used for livestock, poultry, pets and the like, the activecompounds of the formula (1) can be used as formulations (for examplepowders, emulsions, flowables) which comprise the active compounds in anamount of 1 to 80% by weight, directly or after 100 to 10,000-folddilution, or they can be used as a chemical bath.

[0407] It has furthermore been found that the compounds of the formula(I) according to the invention display a high insecticidal actionagainst insects which destroy industrial materials.

[0408] The following insects may be mentioned as examples andpreferred—but without being limiting:

[0409] Beetles, such as

[0410]Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex,Emobius mollis, Priobium carpini, Lyctus bnmneus, Lyctus africanus,Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec, Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec. and Dinoderus minutus.

[0411] Hymenopterons, such as

[0412]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus andUrocerus augur.

[0413] Termites, such as

[0414]Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Reticulitennes flavipes, Reticulitermes santonensis,Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsisnevadensis and Coptotermes formosanus.

[0415] Bristletails, such as

[0416]Lepisma saccharina.

[0417] Industrial materials in the present connection are to beunderstood as meaning non-living materials, such as, preferably,plastics, adhesives, sizes, papers and cards, leather, wood andprocessed wood products, and lacquers and paints.

[0418] Materials to be protected from insect damage which are quiteparticularly preferred are wood and processed wood products.

[0419] Wood and processed wood products which can be protected by theagents according to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat gangplanks, wooden vehicles,crates, pallets, containers, telegraph poles, wood lagging, woodenwindows and doors, plywood, chipboards, joinery or wood products usedquite generally in house construction or building joinery.

[0420] The active compounds can be used as such or in the form ofconcentrates or generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

[0421] The formulations mentioned can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersing agent and/or binder or fixing agent,water repellant, optionally siccatives and UV stabilizers, and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

[0422] The insecticidal compositions or concentrates used forpreservation of wood and derived timber products comprise the activecompound according to the invention in a concentration of 0.0001 to 95%by weight, in particular 0.001 to 60% by weight.

[0423] The amount of composition or concentrate employed depends on thenature and the occurrence of the insects and on the medium. The optimumamount employed for the use can in each case be determined by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compoundbased on the material to be preserved.

[0424] The solvent and/or diluent used is an organochemical solvent orsolvent mixture and/or an oily or oil-like organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water and, if appropriate, an emulsifierand/or wetting agent.

[0425] The organochemical solvents employed are preferably oily oroil-like solvents having an evaporation number above 35 and a flashpoint above 30° C., preferably above 45° C. Corresponding mineral oilsor aromatic fractions thereof or solvent mixtures containing mineraloil, preferably white spirit, petroleum and/or alkylbenzene, are used assuch water-insoluble, oily and oil-like solvents of low volatility.

[0426] Mineral oils having a boiling range from 170 to 220° C., whitespirit having a boiling range from 170 to 220° C., spindle oil having aboiling range from 250 to 350° C., petroleum or aromatics having aboiling range from 160 to 280° C., terpentine oil and the like areadvantageously employed.

[0427] In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablymonochloronaphthalene, are employed.

[0428] The organic oily or oil-like solvents of low volatility having anevaporation number above 35 and a flash point above 30° C., preferablyabove 45° C., can be replaced in part by organochemical solvents of highor medium volatility, provided that the solvent mixture likewise has anevaporation number above 35 and a flash point above 30° C., preferablyabove 45° C., and that the insecticide/fungicide mixture is soluble orcan be emulsified in this solvent mixture.

[0429] According to a preferred embodiment, some of the organochemicalsolvent or solvent mixture is replaced by an aliphatic polarorganochemical solvent or solvent mixture. Aliphatic organochemicalsolvents containing hydroxyl and/or ester and/or ether groups, such as,for example, glycol ethers, esters or the like, are preferably used.

[0430] Organochemical binders which are used within the context of thepresent invention are the synthetic resins and/or binding drying oilswhich are water-dilutable and/or soluble or dispersible or emulsifiablein the organochemical solvents employed and are known per se, inparticular binders consisting of or comprising an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenolic resin, hydrocarbon resin, such asindene-coumarone resin or silicone resin, drying plant and/or dryingoils and/or binders which dry by physical means and are based on anaturally occurring and/or synthetic resin.

[0431] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Bitumen or bituminoussubstances can also be used as binders in an amount of up to 10% byweight. In addition, dyestuffs, pigments, water-repellant agents, odourcorrectants and inhibitors or corrosion prevention agents and the likewhich are known per se can be employed.

[0432] Preferably, according to the invention, the composition orconcentrate comprises at least one alkyd resin or modified alkyd resinand/or one drying plant oil as an organochemical binder. Alkyd resinshaving an oil content of more than 45% by weight, preferably 50 to 68%by weight, are preferably used according to the invention.

[0433] All or some of the binder mentioned can be replaced by a fixingagent (mixture) or a plasticizer (mixture). These additives are intendedto prevent evaporation of the active compounds and crystallization orprecipitation They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

[0434] The plasticizers originate from the chemical classes of phthalicacid esters, such as dibutyl, dioctyl or benzyl butyl phthalate,phosphoric acid esters, such as tributyl phosphate, adipic acid esters,such as di-(2-ethylhexyl) adipate, stearates, such as butyl stearate oramyl stearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

[0435] Fixing agents are based chemically on polyvinyl alkyl ethers,such as, for example, polyvinyl methyl ether, or ketones, such asbenzophenone or ethylenebenzophenone.

[0436] Water in particular is also a possible solvent or diluent, ifappropriate mixed with one or more of the abovementioned organochemicalsolvents or diluents, emulsifiers and dispersing agents.

[0437] Particularly effective wood preservation is achieved byimpregnation processes on a large industrial scale, for example vacuum,double vacuum or pressure processes.

[0438] If appropriate, the ready-to-use compositions can also compriseother insecticides, and if appropriate also one or more fungicides.

[0439] Possible additional admixing partners are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are an express constituent of the presentapplication.

[0440] Especially preferred admixing partners can be insecticides, suchas chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin,cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl butylcarbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

[0441] The preparation and the use of the active compounds according tothe invention can be seen from the following examples.

EXAMPLE (I-a-1)

[0442]

[0443] At reflux temperature, 24.8 g of the compound of Example (II-2)in 150 ml of anhydrous toluene are added dropwise to 18.4 g (0.16 mol)of potassium tert-butoxide in 63 ml of anhydrous tetrahydrofuran (THF),and the mixture is stirred at reflux for another 1.5 hours. 240 ml ofwater are then added, the phases are separated and the toluene phase isextracted with water. The combined aqueous phases are washed withtoluene and, at 10 to 20° C., acidified with approximately 26 ml ofconc. hydrochloric acid. The precipitated solid is filtered off withsuction, washed and dried. For purification, the product is stirred in amixture of methyl tert-butyl ether (MTB ether) and n-hexane.

[0444] Yield 15.6 g (69% of theory), m.p.: >220° C.

[0445] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (I-a) areobtained: TABLE 2 (I-a)

Ex. iso- No. W X Y Z A B m.p. ° C. mer I-a-2 CH₃ CH₃ CH₃ H CH₃ H 195 αI-a-3 H CH₃ CH₃ H CH₃ H 164 α I-a-4 H CH₃ CH₃ H CH₃ H 196 β I-a-5 C₂H₅C₂H₅ CN H CH₃ H 242 β I-a-6 H Cl Cl H CH₃ H >220 β I-a-7 H Cl CH₃ H CH₃H 194 β I-a-8 Cl CH₃ Cl H CH₃ H >220 β I-a-9 Cl Cl CH₃ H CH₃ H 211 βI-a-10 CH₃ CH₃ CH₃ CH₃ CH₃ H >220 β I-a-11 H CH₃ Cl H CH₃ H >220 βI-a-12 CH₃ CH₃ CN H CH₃ H >220 β I-a-13 CH₃ CH₃ H Cl CH₃ H 210 β I-a-14H CH₃ CH₃ CH₃ CH₃ H >220 β I-a-15 H Cl Br H CH₃ H >220 β I-a-16 CH₃ CH₃Cl H CH₃ H 211 β I-a-17 CH₃ CN CH₃ H CH₃ H >220 β I-a-18 CH₃ CH₃ Br HCH₃ H >220 β I-a-19 Br CH₃ Cl H CH₃ H 210 β I-a-20 H CH₃ H CH₃ CH₃H >220 β I-a-21 Br Br C₂H₅ H CH₃ H >220 β I-a-22 H Cl C₂H₅ H CH₃ H >220β I-a-23 CH₃ CH₃ CH₃ H CH₃ CH₃ >220 α I-a-24 H CH₃ CH₃ H CH₃ CH₃ >220 αI-a-25 H Cl Cl CH₃ CH₃ H >240 β I-a-26 H Cl CH₃ Cl CH₃ H >236 β I-a-27 HCH₃ Cl CH₃ CH₃ H >227 β I-a-28 H Br CH₃ Br CH₃ H >240 β I-a-29 H CH₃ ClCl CH₃ H 206 β I-a-30 Br Br i-C₃H₇ H CH₃ H 233 β I-a-31 Cl Cl Cl H CH₃H >234 β

EXAMPLE (I-b-1)

[0446]

[0447] 2.52 mol (18 mmol) of triethylamine are added to 3.62 g of thecompound of Example (I-a-1) in 70 ml of anhydrous methylene chloride. At0 to 10° C., 1.9 ml (18 mmol) of isobutyryl chloride in 5 ml ofanhydrous methylene chloride are added to this mixture, and stirring iscontinued at room temperature until the reaction has ended. The mixtureis then washed twice with 50 ml of 0.5 N NaOH each time, dried andconcentrated. The residue is recrystallized from MTB ether/n-hexane.

[0448] Yield 1.6 g (35% of theory), m.p.: 209° C.

[0449] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (I-b) areobtained: TABLE 3 (I-b)

Ex. m.p. iso- No. W X Y Z A B R¹ ° C. mer I-b-2 CH₃ CH₃ CH₃ H CH₃ H CH₃176 α I-b-3 CH₃ CH₃ CH₃ H CH₃ H i-C₃H₇ 187 α I-b-4 H CH₃ CH₃ H CH₃ Hi-C₃H₇ α¹⁾ I-b-5 CH₃ CH₃ CH₃ H CH₃ H CH₃ 187 β I-b-6 H CH₃ CH₃ H CH₃ HCH₃ 181 β I-b-7 H CH₃ CH₃ H CH₃ H i-C₃H₇ 211 β I-b-8 H Cl CH₃ H CH₃ Hi-C₃H₇ 155 β I-b-9 Cl Cl CH₃ H CH₃ H i-C₃H₇ 178 β I-b-10 CH₃ Cl Cl H CH₃H i-C₃H₇ 204 β I-b-11 CH₃ CH₃ CH₃ CH₃ CH₃ H i-C₃H₇ >220 β I-b-12 CH₃ CH₃CN H CH₃ H i-C₃H₇ 214 β I-b-13 CH₃ CH₃ CN H CH₃ H t-C₄H₉-CH₂ >220 βI-b-14 H CH₃ CH₃ CH₃ CH₃ H i-C₃H₇ 210 β I-b-15 H Cl Br H CH₃ H i-C₃H₇170 β I-b-16 H Cl Br H CH₃ H t-C₄H₉-CH₂ 194 β I-b-17 H CH₃ Cl H CH₃ Hi-C₃H₇ 178 β I-b-18 CH₃ CN CH₃ H CH₃ H i-C₃H₇ 214 β I-b-19 CH₃ CN CH₃ HCH₃ H t-C₄H₉-CH₂ >220 β I-b-20 CH₃ CH₃ Br H CH₃ H i-C₃H₇ >220 β I-b-21CH₃ CH₃ Br H CH₃ H t-C₄H₉-CH₂ >220 β I-b-22 H Cl C₂H₅ H CH₃ H i-C₃H₇ 179β I-b-23 H Cl C₂H₅ H CH₃ H

152 β I-b-24 H CH₃ CH₃ CH₃ CH₃ H

170 β I-b-25 CH₃ CH₃ Cl H CH₃ H i-C₃H₇ 160 β I-b-26 CH₃ CH₃ Cl H CH₃ Hs-C₄H₉ 200 β I-b-27 H CH₃ H CH₃ CH₃ H i-C₃H₇ 193 β I-b-28 CH₃ CH₃ CH₃ HCH₃ CH₃ i-C₃H₇ 191 α I-b-29 H Cl CH₃ Cl CH₃ H i-C₃H₇ 231 β I-b-30 H CH₃Cl CH₃ CH₃ H i-C₃H₇ 210 β I-b-31 H Br CH₃ Br CH₃ H i-C₃H₇ 214- β 216I-b-32 H Cl Cl CH₃ CH₃ H i-C₃H₇ 202- β 205 I-b-33 Br Br C₂H₅ H CH₃ Hi-C₃H₇ 217 β I-b-34 CH₃ CH₃ Cl H CH₃ H (CH₃)₂C═CH >248 β I-b-35 Cl Cl ClH CH₃ H i-C₃H₇ 207 β I-b-36 Br Br i-C₃H₇ H CH₃ H i-C₃H₇ 213 β

EXAMPLE (1-c-1)

[0450]

[0451] At 0 to 10° C., 1.2 ml (12 mmol) of ethyl chloroformate in 5 mlof anhydrous methylene chloride are added dropwise to 3.62 g of thecompound of Example (I-a-1) and 1.7 ml (12 mmol) of triethylamine in 70ml of anhydrous methylene chloride, and the mixture is stirred at roomtemperature until the reaction has ended. The mixture is then washed twotimes with 50 ml of 0.5 N NaOH each time, dried and concentrated and theresidue is recrystallized from MTB ether/n-hexane.

[0452] Yield 2.70 g (60% of theory), m.p.: 217° C.

[0453] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (I-c) areobtained: TABLE 4 (I-c)

Ex. m.p. iso- No. W X Y Z A B M R² ° C. mer I-c-2 CH₃ CH₃ CH₃ H CH₃ H OC₂H₅ 201 α I-c-3 H CH₃ CH₃ H CH₃ H O C₂H₅ 122 α I-c-4 H CH₃ CH₃ H CH₃ HO C₂H₅ 197 β I-c-5 CH₃ CH₃ CH₃ CH₃ CH₃ H O C₂H₅ 211 β I-c-6 CH₃ CH₃ CN HCH₃ H O C₂H₅ 229 β I-c-7 H CH₃ CH₃ CH₃ CH₃ H O C₂H₅ 171 β I-c-8 H Cl BrH CH₃ H O C₂H₅ 201 β I-c-9 H CH₃ Cl H CH₃ H O C₂H₅ 198 β I-c-10 CH₃ CNCH₃ H CH₃ H O C₂H₅ 197 β I-c-11 CH₃ CH₃ Br H CH₃ H O C₂H₅ >220 β I-c-12H Cl Cl H CH₃ H O C₂H₅ 171 β I-c-13 H Cl C₂H₅ H CH₃ H O C₂H₅ 196 βI-c-14 CH₃ CH₃ Cl H CH₃ H O C₂H₅ 205 β I-c-15 H CH₃ H CH₃ CH₃ H O C₂H₅185 β I-c-16 CH₃ CH₃ CH₃ H CH₃ CH₃ O C₂H₅ 218 α I-c-17 H Cl CH₃ Cl CH₃ HO C₂H₅ 222 β I-c-18 H CH₃ Cl CH₃ CH₃ H O C₂H₅ 206 β I-c-19 H Br CH₃ CH₃CH₃ H O C₂H₅ 159-160 β I-c-20 Br C₂H₅ Br H CH₃ H O C₂H₅ β

EXAMPLE (II-1)

[0454]

[0455] At 30 to 40° C., 27.8 g of the compound of Example (XXIII-1) in180 ml of methylene chloride are added dropwise to 45.4 g ofconcentrated sulphuric acid, and the mixture is stirred for another 2hours at 30 to 40° C. 64 ml of anhydrous methanol are then addeddropwise, and the mixture is stirred for another 6 hours at 40 to 70° C.The mixture is then poured onto 0.46 kg of ice and extracted withmethylene chloride, and the organic phase is washed with aqueous NaHCO₃solution, dried and concentrated. The residue is recrystallized from MTBether/n-hexane.

[0456] Yield 19.80 g (64% of theory), m.p.: 101° C.

EXAMPLE (II-2)

[0457]

[0458] At 0 to I 0° C., 19.6 g of mesityleneacetyl chloride in 20 ml ofanhydrous THF are added dropwise to 20.98 g of the compound of Example(XIII-1) and 30.8 ml (0.22 mol) of triethylamine in 200 ml of anhydrousTHF, and the mixture is stirred at room temperature until the reactionhas ended. The mixture is filtered off with suction, the filter cake isrinsed and the filtrate is concentrated. The residue is taken up inmethylene chloride, washed with 200 ml 1 N HCl, dried and concentrated.Silica gel column chromatography using cyclohexane/ethyl acetate 2/1gives 24.0 g (72% of theory). ¹H NMR (200 MHz, CDCl₃): δ=1.12 (d, 3H,CH-CH₃ ), 3.51 (α), 3.6 (B) (2s, 2H, CH₂ , CONH, β/α approximately 3:1),3.71, 3.75 (α/β) (2s, 3H, CO₂-CH₃, (β/α 3:1), 6.90 (α), 6.92 (β) (2s,2H, ArH).

[0459] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (II) areobtained: TABLE 5 (II)

Ex. iso- No. W X Y Z A B R⁸ m.p. ° C. mer II-3 H CH₃ CH₃ H CH₃ H CH₃ 71α II-4 H CH₃ CH₃ H CH₃ H CH₃ β¹⁾ II-5 CH₃ CH₃ CH₃ H CH₃ CH₃ CH₃ 106 αII-6 H CH₃ CH₃ H CH₃ CH₃ CH₃ 96 α II-7 C₂H₅ C₂H₅ CN H CH₃ H CH₃ β²⁾ II-8H Cl Cl H CH₃ H CH₃ β³⁾ II-9 H Cl CH₃ H CH₃ H CH₃ β⁴⁾ II-10 CH₃ Cl Cl HCH₃ H CH₃ 125- β 127 II-11 Cl Cl CH₃ H CH₃ H CH₃ 171 β II-12 H Cl C₂H₅ HCH₃ H CH₃ β⁵⁾ II-13 CH₃ CH₃ CN H CH₃ H CH₃ 111 β II-14 CH₃ CH₃ CH₃ CH₃CH₃ H CH₃ 150 β II-15 H CH₃ CH₃ CH₃ CH₃ H CH₃ 122 β II-16 CH₃ CH₃ H ClCH₃ H CH₃ 159 β II-17 H CH₃ Cl H CH₃ H CH₃ 160 β II-18 H CH₃ CH₃ CH₃ CH₃H CH₃ 141 β II-19 H Cl Br H CH₃ H CH₃ 134 β II-20 CH₃ Cl Br H CH₃ H CH₃164 β II-21 CH₃ CH₃ Cl H CH₃ H CH₃ 118 β II-22 CH₃ CN CH₃ H CH₃ H CH₃135 β II-23 CH₃ CH₃ Br H CH₃ H CH₃ 156 β II-24 CH₃ Br Cl H CH₃ H CH₃ 150β II-25 H CH₃ H CH₃ CH₃ H CH₃ 117 β II-26 Br Br C₂H₅ H CH₃ H CH₃ 141 βII-27 Cl Cl Cl H CH₃ H CH₃ 156 β II-28 Br Br i-C₃H₇ H CH₃ H CH₃ 126 βII-29 H Cl Cl CH₃ CH₃ H CH₃ 150- β 152 II-30 H Cl CH₃ Cl CH₃ H CH₃ 118-β 120 II-31 H CH₃ Cl CH3 CH₃ H CH₃ 144- β 146 II-32 H Br CH₃ Br CH₃ HCH₃ 138- β 140 II-33 H CH₃ Cl Cl CH₃ H CH₃ 146 β

EXAMPLE (XIII-1)

[0460]

[0461] At 0 to 5° C., 73.2 ml (0.87 mol) of thionyl chloride are addeddropwise to 92.3 g of the compound of Example (XVI-1) in 870 ml ofanhydrous methanol, and the mixture is stirred at approximately 0° C.for 30 minutes and then at approximately 40° C. overnight. The mixtureis filtered, the filtrate is concentrated and the residue is stirredwith a little MTB ether, the mixture is filtered off with suction andthe filter cake is rinsed and dried.

[0462] Yield 87.0 g (86% of theory), m.p.: >220° C.

EXAMPLE (XVI-1)

[0463]

[0464] 122.8 g of the compound of the example below and 130 g of NaOH in2.5 l of water are heated in an autoclave at 195° C. for 2 hours, thepressure increasing to approximately 20 bar. The mixture is thenconcentrated to approximately ⅓ of its volume, concentrated HCl is addedat 0 to 10° C. until the pH is 5 to 6, the mixture is concentrated, theresidue is boiled with methanol, the mixture is filtered off withsuction and the filtrate is concentrated.

[0465] Yield 92.3 g (86% of theory), m.p.: >220° C.

[0466] Example: Compound of the Formula

[0467] In an autoclave, a mixture comprising 76 g of3-methyl-tetrahydropyran-4-one, 71.9 g (1.468 mol) of sodium cyanide, 96g (1 mol) of ammonium carbonate, 1.32 l of concentrated ammonia solutionand 1.32 l of ethanol is stirred at 120° C. for 3 hours, the internalpressure increasing to approximately 60 bar (prior to heating, ⅔ of thedesired reaction pressure is applied). The mixture is concentrated,dried with toluene, boiled with methanol and filtered off with suction.The mother liquor is concentrated to 400 ml, and further solidcomponents are precipitated by addition of MTB ether and are filteredoff with suction. The mother liquor is concentrated. The combinedresidues are boiled in ethanol, the mixture is filtered off with suction(A) and the filtrate is concentrated (B). (A) and (B) are combined.

[0468] Yield 126.0 g (100% of theory).

EXAMPLE (XXIII-1)

[0469]

[0470] At 0 to 10° C., 21.6 g of mesitylene acetyl chloride in 20 ml ofanhydrous THF are added dropwise to 15.6 g of the compound of Example(XXII-1) and 15.4 ml of triethylamine in 220 ml of anhydrous THF, andthe mixture is stirred at room temperature until the reaction has ended.The mixture is stirred into 0.6 l of ice-water and 0.2 l of 1 N HCl andfiltered off with suction, and the residue is taken up in methylenechloride. The solution is dried and concentrated and the residue isrecrystallized from MTB ether/n-hexane.

[0471] Yield 27.8 g (84% of theory), m.p.: 121° C.

[0472] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (XXIII)are obtained: TABLE 6 (XXIII)

Ex. No. W X Y Z A B m.p. ° C. XXIII-2 H CH₃ CH₃ H CH₃ H 112 XXIII-3 CH₃CH₃ CH₃ H CH₃ CH₃ 127 XXIII-4 H CH₃ CH₃ H CH₃ CH₃ 118

EXAMPLE (XIV-1)

[0473]

[0474] At 70° C., 99.3 g of 2-chloro-4-ethylphenylacetic acid and 109 ml(1.5 mol) of thionyl chloride are stirred until the evolution of gas hasended. Excess thionyl chloride is removed at 50° C. under reducedpressure. The residue is distilled.

[0475] Yield 99.10 g (91% of theory), b.p. 121° C./0-35 mbar.

EXAMPLE (XVII-1)

[0476]

[0477] 102.5 g (16.9% strength, 0.05 mol) of the compound of Example(XVIII-1), 14.1 g of KOH, 17.8 ml of water and 35.5 ml of methanol areheated together under reflux for 5 hours. The mixture is thenconcentrated and the residue is taken up in water. The solution iswashed with ethyl acetate and the aqueous phase is acidified using conc.HCl (pH 1). The precipitate is filtered off with suction and dried.

[0478] Yield 14.4 g (80.6% of theory), m.p.: 140-142° C.

[0479] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (XVII)are obtained: TABLE 7 (XVII)

Ex. No. W X Y Z m.p. ° C. XVII-2 Br Cl C₂H₅ H 147 XVII-3 Cl Cl C₂H₅ H146 XVII-4 H Cl C₂H₅ H 89-91 XVII-5 H Br C₂H₅ H 109 XVII-6 Br Br i-C₃H₇H 154-155 XVII-7 H CH₃ Cl Cl 103

EXAMPLE (XVIII-1)

[0480]

[0481] With cooling, 9.1 ml of 30% strength sodium methoxide are addeddropwise to 5 g (94.4% strength, 0.0119 mol) of the compound of Example(XIX-1) in 5 ml of methanol, and the mixture is stirred under reflux for5 hours. After cooling, 0.01 ml of concentrated sulphuric acid are addeddropwise, and the mixture is stirred under reflux for 1 hour. Themixture is then concentrated and the residue is taken up in water. Thesolution is extracted with methylene chloride, dried and concentrated.

[0482] Yield 1.80 g (43% of theory), oil.

[0483] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (XVIII)are obtained: TABLE 8 (XVIII)

Ex. No. W X Y Z R⁸ b.p. ° C. (mbar) XVIII-2 Br Cl C₂H₅ H CH₃ 105 0.06XVIII-3 Cl Cl C₂H₅ H CH₃ 92-94 0.05 XVIII-4 H Cl C₂H₅ H CH₃ 82 0.03XVIII-5 H Br C₂H₅ H CH₃ 135 0.15 XVIII-6 Br Br i-C₃H₇ H CH₃ oil* XVIII-7H CH₃ Cl Cl CH₃ oil*

EXAMPLE (XIX-1)

[0484]

[0485] 1400 ml (17.4 mol) of 1,1-dichloroethane and then 320 g (1.147mol) of the compound of Example (XX-1) in 342 ml of anhydrousacetonitrile are added dropwise to 208 ml (1.746 mol) of butyl nitritein 684 ml of anhydrous acetonitrile. The mixture is stirred at roomtemperature overnight and then poured into 4.6 l of 20% strength HCl.The mixture is extracted with MTB ether and the organic phase is washedwith 2 l of water, dried and concentrated.

[0486] Yield 434 g. The crude product reacted further without anyfurther purification.

[0487] Similar to this method, and/or according to the generalpreparation procedures, the following compounds of the formula (XIX) areobtained: TABLE 9 (XIX)

Ex. No. W X Y Z XIX-2 Br Cl C₂H₅ H oil* XIX-3 Cl Cl C₂H₅ H oil* XIX-4 HCl C₂H₅ H oil* XIX-5 H Br C₂H₅ H GC/MS: 314, 316, 318 12%, 14%, 12% 199(100%) 197 (98%) XIX-6 Br Br i-C₃H₇ H oil* XIX-7 H CH₃ Cl Cl oil*

EXAMPLE (XX-1)

[0488]

[0489] At 10-30° C., 397 g (2.48 mol) of bromine in 744 ml of glacialacetic acid are added dropwise to 150 g (1.24 mol) of 4-ethylaniline in1990 ml of glacial acetic acid, and the mixture is stirred at 30° C. foranother 3 hours. The mixture is then diluted with water and madealkaline using 25% strength ammonia solution. The precipitate isfiltered off with suction, taken up in methylene chloride, dried andconcentrated.

[0490] Yield 320.0 g (93% of theory), m.p.: 74° C.

EXAMPLE (XX-2)

[0491] Using the method of Example (XX-1) the compound of the formula

[0492] is obtained

[0493] M.p.: 48° C.

EXAMPLE (XXII-1)

[0494]

[0495] At room temperature, 30.5 g (0.27 mol) of2-methyl-tetrahydropyran-4-one (preparation see further below) are addeddropwise to a mixture comprising 50.9 g (0.75 mol) of 25% strengthammonia solution, 17.2 g (0.32 mol) of ammonium chloride and 15.7 g(0.32 mol) of sodium cyanide in 48 ml of water and the mixture isstirred at 45° C. overnight. Customary work-up gives 29.1 g (77% oftheory) of the end product as an oil.

EXAMPLE (XXII-2)

[0496]

[0497] This compound is obtained in a similar manner as a brown oil.

[0498] Example: Compound of the Formula

[0499] At a temperature of approximately 100° C., 364.37 g of thecompound of the formula ClCH₂CH₂COCH₂CHClCH₃ (preparation see the nextexample) are added dropwise over a period of approximately 75 minutes to552.72 g (3.54 mol) of NaH₂PO_(4×)2 H₂O and 179.7 g (1.55 mol) of 85%strength o-phosphoric acid in 5500 ml of water, and the mixture isstirred at 100° C. for a further 8 hours.

[0500] The mixture is cooled to approximately 0° C. and 10 molar NaOH isadded dropwise until a pH of 5 to 6 is reached. 1500 ml of methylenechloride are added and the resulting salt is filtered off with suctionand the aqueous phase is extracted 3× with 1000 ml of methylene chlorideeach time. The organic phase is dried, concentrated and distilled.

[0501] Yield: 119.6 g (55% of theory), b.p.: 62° C./15 mbar.

[0502] Example: Compound of the Formula ClCH₂CH₂COCH₂CHClCH₃

[0503] At room temperature, 507.88 g of 3-chloropropionyl chloride areadded dropwise over a period of 15 minutes to 758.08 g (5.6 mol) ofAlCl₃ in 560 ml of methylene chloride, and 189 g (4.5 mol) of propyleneare introduced into this mixture at approximately 28 to 30° C. over aperiod of approximately 3 hours.

[0504] The reaction mixture is decanted off from excess AlCl₃ and, at 0to 10° C., slowly added dropwise to a mixture of 508 ml of methylenechloride and 2032 ml of 1 N HCl.

[0505] The organic phase is separated off, washed 3 times with 500 ml ofwater each time, dried and concentrated.

[0506] Yield: 470 g (70% of theory).

USE EXAMPLES

[0507] Example A Myzus test Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycolether

[0508] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0509] Cabbage leaves (Brassica oleracea) which are heavily infested bypeach aphids (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

[0510] After the desired period of time, the kill in % is determined.100% means that all aphids have been killed; 0% means that none of theaphids have been killed.

[0511] In this test, at an exemplary active compound concentration of0.1%, for example the compounds of Examples I-a-9, I-a-10, I-a-12,I-a-14, I-a-15, I-a-16, I-c-8, I-b-17, I-a-18, I-a-19, I-a-20, I-a-21,I-c-11 and I-c-12 effected a kill of in each case 100% after 6 days.

[0512] Example B Nephotettix test Solvent: 20 parts by weight ofdimethylformamide Emulsifier:  1 part by weight of alkylaryl polyglycolether

[0513] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0514] Rice seedlings (Oryzae sativa) are treated by being dipped intothe preparation of active compound of the desired concentration and arepopulated with green rice leaf hoppers (Nephotettix cincticeps) whilethe seedlings are still moist.

[0515] After the desired period of time, the kill in % is determined.100% means that all leaf hoppers have been killed; 0. 1% means that noneof the leaf hoppers have been killed.

[0516] In this test, at an exemplary active compound concentration of0.1%, for example the compounds of Examples I-b-2, I-b-4, I-c-3, I-b-5,I-b-1, I-c-1, I-b-6, I-b-7, I-c-4, I-a7, I-b-8, I-b-11, I-c-5, I-c-7,I-b-17, I-c-11, I-a-22, I-b-22, I-b-23 and I-b-24 effected in each casea kill of 100% after 6 days.

[0517] Example C Phaedon larvae test Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycolether

[0518] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0519] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with larvae of the mustard beetle (Phaedon cochleariae)while the leaves are still moist.

[0520] After the desired period of time, the kill in % is determined.100% means that all beetle larvae have been killed; 0% means that noneof the beetle larvae have been killed.

[0521] In this test, at an exemplary active compound concentration of0.1%, for example the compounds of Examples I-b-8, I-b-22, I-b-23,I-c-13, I-b-4, I-c-3, I-a-7 and I-a-8 effected a kill of in each case100% after 7 days.

[0522] Example D Spodoptera frugiperda test Solvent: 7 parts by weightof dimethylformamide Emulsifier: 1 part by weight of alkylarylpolyglycol ether

[0523] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0524] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the owlet moth (Spodopterafrugiperda) while the leaves are still moist.

[0525] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0526] In this test, at an exemplary active compound concentration of0.1%, for example the compounds of Examples I-c-3, I-a-14, I-c-15,I-a-20, I-c-13 and I-b-24 effected a kill of in each case 100% after 7days.

[0527] Example E Tetranychus test (OP-resistant/dip treatment) Solvent:3 parts by weight of dimethylformamide Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

[0528] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0529] Bean plants (Phaseolus vulgaris) which are heavily infested byall stages of the greenhouse red spider mite Tetranychus urticae aredipped into a preparation of active compound of the desiredconcentration.

[0530] After the desired period of time, the kill in % is determined.100% means that all spider mites have been killed; 0% means that none ofthe spider mites have been killed.

[0531] In this test, at an exemplary active compound concentration of0.1%, for example the compounds of Examples I-b-2, I-b-3, I-b-4, I-c-3,I-a-4, I-c-1, I-b-7, I-c-4, I-a-7, I-a-9 and I-b-8 had an effect of ineach case 100% after 14 days, and the compounds of Examples I-b-15,I-b-16, I-b-17, I-b-22 and I-c-13 had this effect at an exemplary activecompound concentration of 0.02%.

[0532] Example F Critical concentration test/root-systemic action Testinsect: Aphis fabae Solvent: 4 parts by weight of acetone Emulsifier: 1part by weight of alkylaryl polyglycol ether

[0533] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0534] The preparation of active compound is intimately mixed with soil.The concentration of the active compound in the preparation is ofpractically no importance here, only the amount by weight of activecompound per unit volume of soil, which is given in ppm (=mg/l), beingdecisive. The treated soil is transferred into pots and these areplanted with pregerminated broad beans. The active compound can in thisway be taken up from the soil by the roots of the plants and betransported into the leaves.

[0535] To demonstrate the root-systemic effect, the leaves are populatedwith the above-mentioned test animals after 7 days. After a further 6days, evaluation is carried out by counting or estimating the deadanimals. The root-systemic action of the active compound is deduced fromthe mortality figures. It is 100% if all the test animals have beenkilled and 0% if just as many test insects are still alive as in thecase of the untreated control.

[0536] In this test, at an exemplary active compound concentration of 20ppm, for example the compounds of Examples I-a-1, I-b-4, I-a-4, I-b-5,I-a-16, I-b-1, I-b-3, I-c-1, I-c-2, I-b-17, I-b-10, I-a-16 and I-b-25had an effect of in each case 100%.

[0537] Example G Critical concentration test/root-systemic action Testinsect: Myzus persicae Solvent: 4 parts by weight of acetone Emulsifier:1 part by weight of alkylaryl polyglycol ether

[0538] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0539] The preparation of active compound is intimately mixed with soil.The concentration of the active compound in the preparation is ofpractically no importance here, only the amount by weight of activecompound per unit volume of soil, which is given in ppm (=mg/1), beingdecisive. The treated soil is transferred into pots and these areplanted with peppers at the cotyledon stage. The active compound can inthis way be taken up from the soil by the roots of the plants and betransported into the leaves.

[0540] To demonstrate the root-systemic effect, the leaves are populatedwith the above-mentioned test animals after 7 days. After a further 6days, evaluation is carried out by counting or estimating the deadanimals. The root-systemic action of the active compound is deduced fromthe mortality figures. It is 100% if all the test animals have beenkilled and 0% if just as many test insects are still alive as in thecase of the untreated control.

[0541] In this test, at an exemplary active compound concentration of 20ppm, for example the compounds of Examples I-b-10, I-a-16 and I-b-25 hadan effect of in each case 100%.

1. Compounds of the formula (I)

in which W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl,alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy or represents phenyl,phenoxy, phenylthio, phenylalkoxy or phenylalkylthio, each of which isoptionally substituted, X represents halogen, alkyl, alkenyl, alkinyl,alkoxy, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy,cyano, nitro or represents phenyl, phenoxy, phenylthio,. phenylalkyloxyor phenylalkylthio, each of which is optionally substituted, Yrepresents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro, Z represents hydrogen, halogen, alkyl,alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro orrepresents phenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, each of whichis optionally substituted, A represents alkyl or optionally substitutedphenyl, B represents hydrogen or alkyl, G represents hydrogen (a) or oneof the radicals

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl orpolyalkoxyalkyl, each of which is optionally substituted by halogen orcyano, or represents cycloalkyl or heterocyclyl, each of which isoptionally substituted by halogen, alkyl or alkoxy, or representsphenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, each ofwhich is optionally substituted, R² represents alkyl, alkenyl,alkoxyalkyl or polyalkoxyalkyl, each of which is optionally substitutedby halogen or cyano, or represents cycloalkyl, phenyl or benzyl, each ofwhich is optionally substituted, R³, R⁴ and R⁵ independently of oneanother each represent alkyl, alkoxy, alkylamino, dialkylamino,alkylthio, alkenylthio or cycloalkylthio, each of which is optionallysubstituted by halogen, or represent phenyl, benzyl, phenoxy orphenylthio, each of which is optionally substituted, R⁶ and R⁷independently of one another each represent hydrogen, represent alkyl,cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each of which is optionallysubstituted by halogen or cyano, represent phenyl or benzyl, each ofwhich is optionally substituted, or together with the linking N atomform a cycle which optionally contains oxygen or sulphur and which isoptionally substituted.
 2. Compounds of the formula (I) according toclaim 1, in which W represents hydrogen, nitro, cyano, halogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl or C₁-C₄-halogenoalkoxy, X represents halogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,C₂-C₆-halogenoalkenyloxy, cyano, nitro or represents phenyl, phenoxy,phenylthio, phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio, each of whichis optionally substituted by halogen, C₁-C₆alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano, Y representshydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, cyano or nitro, Z represents hydrogen, halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,hydroxyl, cyano, nitro or represents phenoxy, phenylthio, thiazolyloxy,pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-C₁-C₄-alkyloxy orphenyl-C₁-C₄-alkylthio, each of which is optionally substituted byhalogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenalkoxy, nitro or cyano, A represents C₁-C₆-alkyl orrepresents phenyl which is optionally substituted by halogen,C₁-C₄-alkyl, C₁-C₄-alkoxy, nitro or cyano, B represents hydrogen orC₁-C₆-alkyl. G represents hydrogen (a) or represents one of the radicals

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,C₁-C₈-alkylthio-C₁-C₈-alkyl or poly-C₁-C₈-alkoxy-C₁-C₈alkyl, each ofwhich is optionally substituted by halogen or cyano, or representsC₃-C₈-cycloalkyl in which optionally one or two not directly adjacentmethylene groups are replaced by oxygen and/or sulphur and which isoptionally substituted by halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy,represents phenyl which is optionally substituted by halogen, cyano,nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl,C₁-C₆-halogenoalkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl, representsphenyl-C₁-C₆-alkyl which is optionally substituted by halogen, nitro,cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl orC₁-C₆-halogenoalkoxy, represents 5- or 6-membered hetaryl having one ortwo hetero atoms selected from the group consisting of oxygen, sulphurand nitrogen which is optionally substituted by halogen or C₁-C₆-alkyl,represents phenoxy-C₁-C₆-alkyl which is optionally substituted byhalogen or C₁-C₆-alkyl or represents 5- or 6-memberedhetaryloxy-C₁-C₆-alkyl having one or two hetero atoms selected from thegroup consisting of oxygen, sulphur and nitrogen which is optionallysubstituted by halogen, amino or C₁-C₆-alkyl. R² representsC₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₂-C₈-alkyl, each of which is optionally substitutedby halogen or cyano, represents C₃-C₈-cycloalkyl which is optionallysubstituted by halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy or represents phenylor benzyl, each of which is optionally substituted by halogen, cyano,nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl orC₁-C₆-halogenoalkoxy, R³ represents C₁-C₈-alkyl which is optionallysubstituted by halogen or represents phenyl or benzyl, each of which isoptionally substituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, R⁴ and R⁵independently of one another represent C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio orC₃-C₈-alkenylthio, each of which is optionally substituted by halogen,or represents phenyl, phenoxy or phenylthio, each of which is optionallysubstituted by halogen, nitro, cyano, C₁-C₄-alkoxy,C₁-C₄-halogenoalkoxy, C₁-C₄-alkylthio, C₁-C₄-halogenoalkylthio,C₁-C₄alkyl or C₁-C₄-halogenoalkyl, R⁶ and R⁷ independently of oneanother represent hydrogen, represent C₁-C₈-alkyl, C₃-C₈-cycloalkyl,C₁-C₈-alkoxy, C₃-C₈-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl, each of which isoptionally substituted by halogen or cyano or represents phenyl orbenzyl, each of which is optionally substituted by halogen, C₁-C₈-alkyl,C₁-C₈-halogenoalkyl or C₁-C₈-alkoxy, or together represent aC₃-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur and which is optionally substituted byC₁-C₆-alkyl.
 3. Compounds of the formula (I) according to claim 1, inwhich W represents hydrogen, nitro, cyano, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl or C₁-C₂-halogenoalkoxy,X represents fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₃-C₄-alkenyloxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,C₂-C₄-halogenoalkenyloxy, cyano, nitro or represents phenyl orbenzyloxy, each of which is optionally substituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano, Y represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro, Z represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, hydroxyl, cyano, nitro or represents phenoxy orbenzyloxy, each of which is optionally substituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano, A represents C₁-C₄-alkyl orrepresents phenyl, B represents hydrogen, methyl or ethyl, G representshydrogen (a) or represents one of the radicals

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆alkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl or poly-C₁-C₆-alkoxy-C₁-C₆alkyl, each ofwhich is optionally substituted by fluorine, chlorine, or representsC₃-C₇-cycloalkyl in which optionally one or two not directly adjacentmethylene groups are replaced by oxygen and/or sulphur and which isoptionally substituted by fluorine, chlorine, C₁-C₅-alkyl orC₁-C₅-alkoxy, represents phenyl, which is optionally substituted byfluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₃-halogenoalkyl, C₁-C₃-halogenoalkoxy, C₁-C₄-alkylthio orC₁-C₄alkylsulphonyl, represents phenyl-C₁-C₄-alkyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₃-halogenoalkyl or C₁-C₃-halogenoalkoxy, represents pyrazolyl,thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which isoptionally substituted by fluorine, chlorine, bromine or C₁-C₄-alkyl,represents phenoxy-C₁-C₈-alkyl which is optionally substituted byfluorine, chlorine, bromine or C₁-C₄-alkyl or representspyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkyl orthiazolyloxy-C₁-C₅-alkyl, each of which is optionally substituted byfluorine, chlorine, bromine, amino or C₁-C₄-alkyl, R² representsC₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₂-C₆-alkyl, each of which is optionally substitutedby fluorine or chlorine, represents C₃-C₇-cycloalkyl which is optionallysubstituted by fluorine, chlorine, C₁-C₄-alkyl or C₁-C₄-alkoxy orrepresents phenyl or benzyl, each of which is optionally substituted byfluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₃-alkoxy,C₁-C₃-halogenoalkyl or C₁-C₃-halogenoalkoxy, R³ represents C₁-C₆-alkylwhich is optionally substituted by fluorine or chlorine or representsphenyl or benzyl, each of which is optionally substituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkoxy,C₁-C₂-halogenoalkyl, cyano or nitro, R⁴and R⁵ independently of oneanother represent C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio or C₃-C₄-alkenylthio, each ofwhich is optionally substituted by fluorine or chlorine, or representphenyl, phenoxy or phenylthio, each of which is optionally substitutedby fluorine, chlorine, bromine, nitro, cyano, C₁-C₃-alkoxy,C₁-C₃-halogenoalkoxy, C₁-C₃-alkylthio, C₁-C₃-halogenoalkylthio,C₁-C₃-alkyl or C₁-C₃-halogenoalkyl. R⁶ and R⁷ independently of oneanother particularly preferably represent hydrogen, representC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl orC₁-C₆-alkoxy-C₂-C₆-alkyl, each of which is optionally substituted byfluorine or chlorine, or represent phenyl or benzyl, each of which isoptionally substituted by fluorine, chlorine, bromine,C₁-C₅-halogenoalkyl, C₁-C₅-alkyl or C₁-C₅-alkoxy, or together representa C₃-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur and which is optionally substituted byC₁-C₄-alkyl.
 4. Compounds of the formula (I) according to claim 1, inwhich W represents hydrogen, nitro, cyano, fluorine, chlorine, bromine,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, methoxy, ethoxy,n-propoxy, isopropoxy, trifluoromethyl, difluoromethoxy ortrifluoromethoxy, X represents fluorine, chlorine, bromine, methyl,ethyl, n-propyl, isopropyl, n-butyl, isobutyl, methoxy, ethoxy,n-propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano or nitro, Y represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl,isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy,trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, Zrepresents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy,n-propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano or nitro, A represents methyl or ethyl, Brepresents hydrogen or methyl, G represents hydrogen (a) or representsone of the radicals

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl,C₁-C₄-alkylthio-C₁-C₆-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl, each ofwhich is optionally substituted by fluorine or chlorine, or representsC₃-C₆-cycloalkyl in which optionally one or two not directly adjacentmethylene groups are replaced by oxygen and/or sulphur and which isoptionally substituted by fluorine, chlorine, methyl, ethyl, n-propyl,i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, n-propoxy orisopropoxy, represents phenyl which is optionally substituted byfluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl,i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy,methylthio, ethylthio, methylsulphonyl or ethylsulphonyl, representsbenzyl which is optionally substituted by fluorine, chlorine, bromine,methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy, represents furanyl, thienyl or pyridyl, each of whichis optionally substituted by fluorine, chlorine, bromine, methyl orethyl, represents phenoxy-C₁-C₄-alkyl which is optionally substituted byfluorine, chlorine, methyl or ethyl or representspyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl orthiazolyloxy-C₁-C₄-alkyl, each of which is optionally substituted byfluorine, chlorine, amino, methyl or ethyl, R² represents C₁-C₁₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₄-alkoxy-C₂-C₆-alkyl, each of which is optionally substitutedby fluorine or chlorine, represents C₃-C₆-cycloalkyl which is optionallysubstituted by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl ormethoxy, or represents phenyl or benzyl, each of which is optionallysubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl,n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl ortrifluoromethoxy, R³ represents methyl, ethyl, n-propyl, isopropyl,n-butyl, tert-butyl, each of which is optionally substituted by fluorineor chlorine, or represents phenyl or benzyl, each of which is optionallysubstituted by fluorine, chlorine, bromine. methyl, ethyl, isopropyl,tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, R⁴ and R⁵ independently of one anotherrepresent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino or C₁-C₄-alkylthio, each of which is optionallysubstituted by fluorine or chlorine, or represent phenyl, phenoxy orphenylthio, each of which is optionally substituted by fluorine,chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl ortrifluoromethoxy and R⁶ and R⁷ independently of one another representhydrogen, represent C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionallysubstituted by fluorine or chlorine, or represent phenyl or benzyl, eachof which is optionally substituted by fluorine, chlorine, bromine,methyl, methoxy or trifluoromethyl, or together represent aC₅-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur and which is optionally substituted bymethyl or ethyl.
 5. Process for preparing compounds of the formula (I)according to claim 1, characterized in that (A) compounds of the formula(I-a)

in which A, B, W, X, Y and Z are each as defined in claim
 1. areobtained when compounds of the formula (II)

in which A, B, W, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl, are intramolecularly condensed in the presence of adiluent and in the presence of a base and, if appropriate subsequently(Bα) reacted with acyl halides of the formula (III)

in which R¹ is as defined in claim 1 and Hal represents halogen or β)reacted with carboxylic anhydrides of the formula (IV)R¹—CO—O—CO—R¹  (IV) in which R¹ is as defined above, if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder; or (C) reacted with chloroformic esters or chloroformicthioesters of the formula (V) R²—M—CO—Cl  (V) in which R² and M are eachas defined in claim 1, if appropriate in the presence of a diluent andif appropriate in the presence of an acid binder; (D) reacted withchloromonothioformic esters or chlorodithioformic esters of the formula(VI)

in which M and R² are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder; or (E) reacted with sulphonyl chlorides of the formula (VII)R³—SO₂—Cl  (VII) in which R³ is as defined in claim 1, if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder; or (F) reacted with phosphorus compounds of the formula (VIII)

in which L, R⁴ and R⁵ are each as defined in claim 1 and Hal represcntshalogen, if appropriate in the presence of a diluent and if appropriatein the presence of an acid binder; or (G) reacted with metal compoundsor amines of the formulae (IX) or (X)

in which Me represents a mono- or divalent metal, t represents thenumber 1 or 2 and R⁹, R¹⁰, R¹¹ independently of one another eachrepresent hydrogen or alkyl, if appropriate in the presence of adiluent; or (Hα) reacted with isocyanates or isothiocyanates of theformula (XI) R⁶—N═C═L  (XI) in which R⁶ and L are each as defined inclaim 1, if appropriate in the presence of a diluent and if appropriatein the presence of a catalyst; or β) reacted with carbamoyl chlorides orthiocarbamoyl chlorides of the formula (XII)

in which L, R⁶ and R⁷ are each as defined in claim 1, if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder.
 6. Compounds of the formula (II)

in which A, B, W, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 7. Compounds of the formula (XIII)

in which A and B are each as defined above and R⁸ represents alkyl. 8.Compounds of the formula (XV)

which A B, W, X, Y and Z are each as defined in claim
 1. 9. Compounds ofthe formula (XVI)

in which A and B are each as defined in claim
 1. 10. Compound of theformula (XXII)

in which A and B are each as defined in claim
 1. 11. Compounds of theformula (XXIII)

in which A, B, X, Y, Z and W are each as defined in claim
 1. 12.Compounds of the formula (XVII)

in which X¹ represents fluorine, chlorine or bromine (in particularchlorine or bromine), Y¹ represents ethyl and W¹ represents hydrogen,fluorine chlorine or bromine (in particular hydrogen, chlorine orbromine).
 13. Compounds of the formula (XVIII)

in which X¹, Y¹ and W¹ are each as defined in claim 9 and R⁸ representsalkyl (in particular C₁-C₆-alkyl, specifically methyl or ethyl). 14.Pesticides or herbicides, characterized in that they contain a compoundof the formula (I) according to claim
 1. 15. The use of compounds of theformula (I) according to claim 1 for controlling pests and weeds. 16.Method for controlling pests and weeds, characterized in that compoundsof the formula (I) according to claim 1 are allowed to act on pests orweeds and/or their habitat.
 17. Process for preparing pesticides andherbicides, characterize in that compounds of the formula (I) accordingto claim 1 are mixed with extenders and/or surfactants.